Methyl 1-methylindazole-6-carboxylate synthesis
- Product Name:Methyl 1-methylindazole-6-carboxylate
- CAS Number:1007219-73-9
- Molecular formula:C10H10N2O2
- Molecular Weight:190.2
170487-40-8
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74-88-4
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1007219-73-9
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1071433-01-6
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Yield:1007219-73-9 130 mg ，1071433-01-6 230 mg
Reaction Conditions:
Stage #1:1H-indazole-6-carboxylic acid methyl ester with sodium hydride in mineral oil at 20; for 0.5 h;Cooling with ice;
Stage #2:methyl iodide in mineral oilOverall yield = 59 %;
Steps:
4 PREPARATION 4: Methyl 1 -methyl- lH-indazole-6-carboxylate and methyl 2- methyl-2H-indazole-6-carbox late
S[00478] To an ice-cooled solution of methyl lH-indazole-6-carboxylate (566 mg, 3.21 mmol) was added NaH (154 mg, 3.85 mmol), the mixture was then stirred at room temperature for 30min. Methyl iodide (547 mg, 3.85 mmol) was added drop wise, and the reaction mixture was stirred overnight. Cooled to 0 °C, added water and extracted with ethyl acetate. The organic phase was concentrated and purified by gel chromatograph to provide 130 mg of methyl 1 -methyl- lH-indazole-6-carboxyl ate and 230 mg of methyl 2 -methyl -2H-indazole-6- carboxylate, 59%.1H NMR for methyl 1 -methyl- lH-indazole-6-carboxylate: 1H NMR (400 MHz, CDC13): δ 3.97 (3H, s), 4.14 (3H, s), 7.74-7.82 (2H, m), 8.02 (1H, s), 8.17 (1H, d, J = 0.8 Hz). 1H NMR for methyl 2-methyl-2H-indazole-6-carboxylate: 1H NMR (400 MHz, CDC13): δ 3.94 (3H, s), 4.25 (3H, s), 7.65-7.72 (2H, m), 7.92 (1H, s), 8.47 (1H, d, J= 1.2 Hz). [M+H] Calc'd for C 10H10N2O2, 191; Found, 191.
References:
QUANTICEL PHARMACEUTICALS, INC;NIE, Zhe;STAFFORD, Jeffrey, Alan;VEAL, James, Marvin;WALLACE, Michael, Brennan WO2014/89364, 2014, A1 Location in patent:Paragraph 00477; 00478
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590417-94-0
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1007219-73-9
69 suppliers
$31.00/250mg
170487-40-8
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$6.00/250mg
74-88-4
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$15.00/10g
1007219-73-9
69 suppliers
$31.00/250mg
57848-46-1
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1007219-73-9
69 suppliers
$31.00/250mg