Chloroacetone → 1H-Pyrazolo(4,3-b)pyridine

HRID 1257061Notes

Reaction equation

HRID 1257061 reaction equation
[N:1]1[N:2]([CH2:10][C:11](=[O:13])[CH3:12])[CH:3]=[C:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[N:5]2.ClCC(=O)C.C(=O)([O-])[O-].[K+].[K+].[NH:25]1[C:33]2[C:28](=[N:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[N:26]1.[NH2:34]C1C(C)=NC=CC=1>>[NH2:34][C:11]([CH3:12])([CH2:10][N:2]1[CH:3]=[C:4]2[N:5]=[CH:6][CH:7]=[CH:8][C:9]2=[N:1]1)[C:33]#[N:25].[N:1]1[N:2]([CH2:10][C:11](=[O:13])[CH3:12])[CH:3]=[C:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[N:5]2.[NH:25]1[C:33]2[C:28](=[N:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[N:26]1

Participants

8

Reactant 5

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 5726163-Amino-2-methylpyridineHCID 216436531H-Pyrazolo(4,3-b)pyridineHCID 68710470HCID 68710470, compound

Product 3

HCID 216436531H-Pyrazolo(4,3-b)pyridineYield 34%HCID 68707040HCID 68707040, compoundHCID 68710470HCID 68710470, compoundYield 6.6%

Procedure

Using a procedure similar to that described in Example 1, except using 2-amino-2-methyl-3-(2H-pyrazolo[4,3-b]pyridin-2-yl)-propionitrile (27 mg), the title compound was isolated as a white solid (8 mg). MS (ES): M/Z [M+H]=390. 1H NMR: (400 MHz, CHLOROFORM-d): 1.94 (s, 3H), 4.87 (d, J=14.1 Hz, 1H), 5.04 (d, J=14.1 Hz, 1H), 7.31 (d, J=7.6 Hz, 3H), 7.90 (d, J=8.8 Hz, 2H), 8.05 (d, J=8.8 Hz, 1H), 8.30 (s, 1H), 8.43 (s, 1H) and 8.65 (d, J=2.9 Hz, 1H). 19F NMR (376 MHz, CHLOROFORM-d): −58.1 (s, 3F). 2-Amino-2-methyl-3-(2H-pyrazolo[4,3-b]pyridin-2-yl)-propionitrile (37 mg) was prepared using a procedure similar to that described in Example 1, part b, except starting from 1-(2H-pyrazolo[4,3-b]pyridin-2-yl)propan-2-one (37 mg). 1-(2H-Pyrazolo[4,3-b]pyridin-2-yl)propan-2-one (37 mg, 6.6%; MS (ES): M/Z [M+H]=176) was prepared using a procedure similar to that described in Example 182 part g using chloroacetone and potassium carbonate except starting from 1H-pyrazolo[4,3-b]pyridine (380 mg). 1H-pyrazolo[4,3-b]pyridine (380 mg, 34%) was prepared using a procedure similar to that described in Example 182 part f except starting from 3-amino-2-methylpyridine (1 g).

Sources & evidence

ORD record
ord-1d9f36ca01ee49d9a93559bdd58b7cf1
Source dataset
uspto-grants-2013_06
Patent number
US08461176B2

Reaction notes

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