Sodium Carbonate → HCID 57965021, compound

HRID 1931657Notes

Reaction equation

HRID 1931657 reaction equation
[F:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([OH:11])[CH:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([N:25]2[C:29]3=[N:30][CH:31]=[N:32][C:33](Cl)=[C:28]3[CH:27]=[N:26]2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[C:12]([O:16][C:17]([N:19]1[CH2:20][CH2:21][CH:22]([N:25]2[C:29]3=[N:30][CH:31]=[N:32][C:33]([O:11][C:4]4[CH:3]=[C:2]([F:1])[C:9]([F:10])=[CH:8][C:5]=4[C:6]#[N:7])=[C:28]3[CH:27]=[N:26]2)[CH2:23][CH2:24]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 231489854,5-Difluoro-2-hydroxybenzonitrileHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2×

Product 1

HCID 57965021HCID 57965021, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4,5-difluoro-2-hydroxy-benzonitrile (Lancaster Synthesis Ltd. (Lancashire, UK; 14 mg, 0.089 mmol), 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 30 mg, 0.089 mmol), and potassium carbonate (27 mg, 0.196 mmol) in dimethylformamide (1 mL) was heated in a microwave oven at 160° C. for 10 min. Saturated sodium carbonate solution was added to the reaction mixture, and the mixture was then filtered through a pad of silica gel to remove the precipitate. The silica gel pad was washed with methanol and the solvents were evaporated from the filtrate. The residue was purified by HPLC to give 4-[4-(2-cyano-4,5-difluoro-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (5 mg, 13%) as a white solid.

Workup

  1. customLancaster Synthesis Ltd
  2. filtrationthe mixture was then filtered through a pad of silica gel
  3. customto remove the precipitate
  4. washThe silica gel pad was washed with methanol
  5. customthe solvents were evaporated from the filtrate
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-19f23ded9b674d6d932dc49adb8763fe
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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