Water → HCID 58086665, compound

HRID 1965002Notes

Reaction equation

HRID 1965002 reaction equation
[F:1][C:2]1[C:7]([CH2:8][C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:16]=3)[N:11]([Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])[CH:10]=2)=[C:6]([F:34])[CH:5]=[CH:4][C:3]=1[OH:35].[H-].[Na+].Br[CH2:39][C:40]([O:42][CH3:43])=[O:41].O>O1CCCC1>[CH3:43][O:42][C:40](=[O:41])[CH2:39][O:35][C:3]1[CH:4]=[CH:5][C:6]([F:34])=[C:7]([CH2:8][C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:16]=3)[N:11]([Si:24]([CH:28]([CH3:29])[CH3:30])([CH:31]([CH3:33])[CH3:32])[CH:25]([CH3:26])[CH3:27])[CH:10]=2)[C:2]=1[F:1]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 58087617HCID 58087617, compound

Product 1

HCID 58086665HCID 58086665, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2,4-Difluoro-3-(5-pyridin-3-yl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-phenol (549, 427.0 mg, 0.87 mmol) in tetrahydrofuran (20.0 mL) was added sodium hydride (60% in mineral oil, 42.0 mg, 1.1 mmol). 30 minutes later, methyl bromoacetate (146 mg, 0.95 mmol) was added to the reaction. The reaction was stirred at room temperature for 4 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to give the crude compound that was used directly in the next step.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-03f43f2064dc438c96dcd0944b73a17d
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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