Water → [3-(2-Chloro-4-methanesulfonyl-benzyloxy)-2-ethoxy-phenyl]-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

HRID 1098533Notes

Reaction equation

HRID 1098533 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:5]=1[C:11]([C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[N:15]([Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH:14]=1)=[O:12])[CH3:2].[H-].[Na+].Br[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([S:42]([CH3:45])(=[O:44])=[O:43])=[CH:38][C:37]=1[Cl:46].O>O1CCCC1>[Cl:46][C:37]1[CH:38]=[C:39]([S:42]([CH3:45])(=[O:44])=[O:43])[CH:40]=[CH:41][C:36]=1[CH2:35][O:10][C:9]1[C:4]([O:3][CH2:1][CH3:2])=[C:5]([C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[N:15]([Si:22]([CH:23]([CH3:24])[CH3:25])([CH:29]([CH3:30])[CH3:31])[CH:26]([CH3:28])[CH3:27])[CH:14]=2)=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27610831-(Bromomethyl)-2-chloro-4-(methylsulfonyl)benzeneHCID 58086092(2-ethoxy-3-hydroxy-phenyl)-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

Product 1

HCID 58087362[3-(2-Chloro-4-methanesulfonyl-benzyloxy)-2-ethoxy-phenyl]-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-ethoxy-3-hydroxy-phenyl)-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (665, 40 mg, 0.064 mmol) in tetrahydrofuran (15 mL) was added sodium hydride (3.32 mg, 0.083 mmol) at room temperature under an atmosphere of nitrogen. The mixture was stirred at room temperature for 40 minutes, then 1-bromomethyl-2-chloro-4-methanesulfonyl-benzene (21.72 mg, 0.077 mmol) was added to the reaction mixture. It was stirred at room temperature overnight. The mixture was then poured into water and was extracted with ethyl acetate. The organic layer was collected and washed with brine, dried over magnesium sulfate. After removal of the solvent, a crude compound as light yellow oil was obtained (666, 84 mg).

Workup

  1. stirringIt was stirred at room temperature overnight
  2. extractionwas extracted with ethyl acetate
  3. customThe organic layer was collected
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter removal of the solvent

Sources & evidence

ORD record
ord-2d593a4c1d5d4b12aaf4a1fab579bd2a
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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