Sodium Bicarbonate → N-Phenyl-N'-{4-[4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl]phenyl}urea

HRID 28870Notes

Reaction equation

HRID 28870 reaction equation
Br[C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:20])=[CH:14][CH:13]=2)=[N:4][N:5]([CH2:7][C:8]([F:11])([F:10])[F:9])[CH:6]=1.CC1(C)C(C)(C)OB([C:36]2[CH:41]=[CH:40][N:39]=[C:38]3[NH:42][CH:43]=[CH:44][C:37]=23)O1.C(=O)(O)[O-].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C)C=O>[C:22]1([NH:21][C:19]([NH:18][C:15]2[CH:16]=[CH:17][C:12]([C:3]3[C:2]([C:36]4[CH:41]=[CH:40][N:39]=[C:38]5[NH:42][CH:43]=[CH:44][C:37]=45)=[CH:6][N:5]([CH2:7][C:8]([F:11])([F:10])[F:9])[N:4]=3)=[CH:13][CH:14]=2)=[O:20])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 497588714-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 68995186N-{4-[4-bromo-1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl]phenyl}-N'-phenylurea

Product 1

HCID 46888609N-Phenyl-N'-{4-[4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl]phenyl}ureaYield 35%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-{4-[4-bromo-1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl]phenyl}-N′-phenylurea (0.059 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (0.059 mmol), tetrakis(triphenylphosphine)palladium(0) (0.003 mmol), saturated sodium bicarbonate (0.177 mL) and anhydrous N,N-dimethylformamide (1 mL) was stirred at 100° C. in a sealed tube for 4 h and cooled to room temperature. Filtration through a pad of Celite, concentration in vacuo and Gilson reverse phase HPLC purification furnished the title compound as a white solid (35%). ESMS [M+H]+: 477.2

Workup

  1. temperaturecooled to room temperature
  2. filtrationFiltration
  3. concentrationthrough a pad of Celite, concentration
  4. customin vacuo and Gilson reverse phase HPLC purification

Sources & evidence

ORD record
ord-82c4b54e3079474f84e7b6e6ace78bae
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

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