1-{4-[1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-ethanone → 2-{4-[1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-propan-2-ol

HRID 1515890Notes

Reaction equation

HRID 1515890 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:20]([C:27]2[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[CH:29][CH:28]=2)=[CH:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:36][Mg]Cl>O1CCCC1.[Cl-].[Na+].O>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:20]([C:27]2[CH:28]=[CH:29][C:30]([C:33]([OH:35])([CH3:36])[CH3:34])=[CH:31][CH:32]=2)=[CH:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 672287081-{4-[1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-ethanoneHCID 178418332HCID 178418332, compound

Product 1

HCID 672292072-{4-[1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-propan-2-olYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-{4-[1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-ethanone (210 mg, 0.43 mmol) in anhydrous tetrahydrofuran (5 mL) at 0° C. was added methylmagnesium chloride in tetrahydrofuran (3 M, 0.43 ml, 1.29 mmol) dropwise. After stirring for 2 h at 0° C., the reaction mixture was poured into brine (15 mL), extracted with ethyl acetate (2×50 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by flash column chromatography (silica gel from QingDao, 200-300 mesh, 33% ethyl acetate/hexanes) afforded 2-{4-[1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-propan-2-ol (220 mg, 100%): LC/MS m/e calcd for C29H29FN2O3S [M+H]+ 505.63, observed 505.2.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by flash column chromatography (silica gel from QingDao, 200-300 mesh, 33% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-55ba72c567ad4e48a1403d6c6ffb0b41
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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