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18162-48-6872-50-4Methylene ChloridenaphthaleneTHFTitanium Dioxide
877994-06-4

5-Methoxypyrazolo[1,5-a]pyridine synthesis

4synthesis methods
PYRAZOLO[1,5-A]PYRIDIN-5-OL

156969-42-5
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Iodomethane

74-88-4
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$15.00/10g

5-Methoxypyrazolo[1,5-a]pyridine

877994-06-4
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Yield:877994-06-4 86%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide; for 3 h;

Steps:

4.1.2.23. 5-Methoxypyrazolo[1,5-a]pyridine-3-carbaldehyde (4aa)24

Decarboxylation of 3aa (114 mg, 0.52 mmol) gave pyrazolo[1,5-a]pyridin-5-ol (7ab) as a pale brown solid (61 mg, 88%). 1H NMR δ (400 MHz, d6-DMSO) 10.06 (s, 1H), 8.45 (d, J = 7.5 Hz, 1H), 7.79 (d, J = 2.2 Hz, 1H), 6.77 (d, J = 2.4 Hz, 1H), 6.46 (dd, J = 7.5, 2.4 Hz, 1H), 6.23 (d, J = 2.2 Hz, 1H). LC-MS (APCI+) 135 (MH+, 100%). Iodomethane (23 μL, 0.37 mmol) was added to a suspension of 7ab (25 mg, 0.19 mmol) and K2CO3 (52 mg, 0.38 mmol) in DMF (2 mL). After 3 h, the reaction mixture was diluted with water and extracted twice with CH2Cl2. The combined extracts were dried (Na2SO4) and the solvent removed in vacuo to leave 5-methoxypyrazolo[1,5-a]pyridine (7aa) as a pale brown oil (24 mg, 86%). 1H NMR δ (400 MHz, CDCl3) 8.28 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 2.2 Hz, 1H), 6.74 (d, J = 2.7 Hz, 1H), 6.44 (dd, J = 7.6, 2.7 Hz, 1H), 6.32 (d, J = 2.2 Hz, 1H), 3.84 (s, 3H). LC-MS (APCI+) 149 (MH+, 100%). Vilsmeier reaction of 7aa (24 mg, 0.16 mmol) gave 4aa as a pale yellow solid (27 mg, 93%).

References:

Kendall, Jackie D.;O'Connor, Patrick D.;Marshall, Andrew J.;Frédérick, Rapha?l;Marshall, Elaine S.;Lill, Claire L.;Lee, Woo-Jeong;Kolekar, Sharada;Chao, Mindy;Malik, Alisha;Yu, Shuqiao;Chaussade, Claire;Buchanan, Christina;Rewcastle, Gordon W.;Baguley, Bruce C.;Flanagan, Jack U.;Jamieson, Stephen M.F.;Denny, William A.;Shepherd, Peter R. [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 1,p. 69 - 85] Location in patent:experimental part

99446-31-8 Synthesis
methyl 5-methoxyH-pyrazolo[1,5-a]pyridine-3-carboxylate

99446-31-8
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5-Methoxypyrazolo[1,5-a]pyridine

877994-06-4
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References
620-08-6 Synthesis
4-Methoxypyridine

620-08-6
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5-Methoxypyrazolo[1,5-a]pyridine

877994-06-4
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References
99446-53-4 Synthesis
5-METHOXY-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER

99446-53-4
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$80.00/1g

5-Methoxypyrazolo[1,5-a]pyridine

877994-06-4
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References