ChemicalBook CAS DataBase List Methyl 1-methylindazole-6-carboxylate

Methyl 1-methylindazole-6-carboxylate synthesis

4synthesis methods

Product Name:Methyl 1-methylindazole-6-carboxylate
CAS Number:1007219-73-9
Molecular formula:C10H10N2O2
Molecular Weight:190.2

170487-40-8 Synthesis

170487-40-8
201 suppliers
$6.00/250mg

74-88-4
342 suppliers
$15.00/10g

1007219-73-9
62 suppliers
$31.00/250mg

1071433-01-6
58 suppliers
$9.00/100mg

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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67-56-1 Synthesis