Water → HCID 67209758, compound

HRID 402503Notes

Reaction equation

HRID 402503 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]2[NH:9][C:10](=[O:17])[CH:11]=[C:12]([C:13]([F:16])([F:15])[F:14])[C:7]=2[C:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:5]1.Br[CH2:25][C:26]([O:28]CC)=[O:27].O>CN(C=O)C>[CH3:3][N:4]1[C:8]2=[N:9][C:10]([O:17][CH2:25][C:26]([OH:28])=[O:27])=[CH:11][C:12]([C:13]([F:14])([F:16])[F:15])=[C:7]2[C:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 67209859HCID 67209859, compound

Product 1

HCID 67209758HCID 67209758, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (23 mg, 0.56 mmol) was added to a stirred solution of 1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-6(7H)-one (41 mg, 0.14 mmol) in DMF (4 ml) and the resulting mixture was stirred for 30 min. Then ethyl bromoacetate (47 mg, 6.50 mmol) was added and the mixture was stirred for additional 1 h. To the mixture water (0.5 ml) was added and stirred for 2 h. The reaction mixture was concentrated. 1N aqueous HCL was added to the mixture and the solution was extracted with diethyl ether. The organic layer was washed with water and brine, filtered and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure. The crude product was purified by flash column chromatography (80% EtOAc in hexane) to yield the title compound (29 mg, 59%) [1H-NMR (CDCl3, 300 MHz) δ 7.45-7.30 (m, 5H), 7.05 (s, 1H), 7.00 (s, 1H), 5.03 (s, 2H), 3.81 (s, 3H); LCMS RtE=1.94 min; [M+H]+=351.0]

Workup

  1. stirringthe mixture was stirred for additional 1 h
  2. stirringstirred for 2 h
  3. concentrationThe reaction mixture was concentrated
  4. addition1N aqueous HCL was added to the mixture
  5. extractionthe solution was extracted with diethyl ether
  6. washThe organic layer was washed with water and brine
  7. filtrationfiltered
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationThe organic layer was concentrated under reduced pressure
  10. customThe crude product was purified by flash column chromatography (80% EtOAc in hexane)

Sources & evidence

ORD record
ord-ea49ead7ee4d4abbbf7c0b0381756ae7
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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