Sodium hydride → 2-(7-chloro-6-fluoro-2H-pyrazolo[4,3-b]pyridin-2-yl)-N-methylacetamide

HRID 1522651Notes

Reaction equation

HRID 1522651 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[CH:9]=[N:10][NH:11][C:3]=12.[H-].[Na+].Br[CH2:15][C:16]([NH:18][CH3:19])=[O:17]>C1COCC1>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[CH:9]=[N:10][N:11]([CH2:15][C:16]([NH:18][CH3:19])=[O:17])[C:3]=12.[Cl:1][C:2]1[C:3]2[C:4](=[CH:9][N:10]([CH2:15][C:16]([NH:18][CH3:19])=[O:17])[N:11]=2)[N:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 154907452-Bromo-N-methylacetamideHCID 674705117-chloro-6-fluoro-1H-pyrazolo[4,3-b]pyridine

Product 2

HCID 674696412-(7-chloro-6-fluoro-2H-pyrazolo[4,3-b]pyridin-2-yl)-N-methylacetamideHCID 674704132-(7-chloro-6-fluoro-1H-pyrazolo[4,3-b]pyridin-1-yl)-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-Chloro-6-fluoro-1H-pyrazolo[4,3-b]pyridine (100 mg, 0.583 mmol) and NaH (28.0 mg, 60% in oil, 0.699 mmol) in THF (2.0 mL) was stirred at 0° C. for 15 minutes. 2-Bromo-N-methylacetamide (89 mg, 0.583 mmol) was added and the reaction was allowed to warm to room temperature for 12 hours. The reaction mixture was then concentrated in vacuo to give 2-(7-chloro-6-fluoro-1H-pyrazolo[4,3-b]pyridin-1-yl)-N-methylacetamide and 2-(7-chloro-6-fluoro-2H-pyrazolo[4,3-b]pyridin-2-yl)-N-methylacetamide which were used without further purification.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-06a195f985a547a3b44260b56510e0a1
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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