HCID 67229219, compound → HCID 67227818, compound

HRID 1515668Notes

Reaction equation

HRID 1515668 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:21]([C:28]2[CH:33]=[CH:32][C:31]([C:34](=[O:36])[CH3:35])=[CH:30][CH:29]=2)=[CH:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:37][Mg]Cl>O1CCCC1>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:21]([C:28]2[CH:29]=[CH:30][C:31]([C:34]([OH:36])([CH3:37])[CH3:35])=[CH:32][CH:33]=2)=[CH:22][CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 67229219HCID 67229219, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 67227818HCID 67227818, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1-{4-[1-(1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-ethanone (300 mg, 0.6 mmol) in dry tetrahydrofuran (5 mL) was added a methylmagnesium chloride solution in tetrahydrofuran (3 M, 2 mL, 6 mmol) at 0° C. The resulting mixture was stirred at room temperature for 2 h, quenched with an ammonium chloride solution, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 25% ethyl acetate/hexanes) afforded 2-{4-[1-(1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-propan-2-ol (160 mg, 51.8%) as a light yellow solid: LC/MS m/e calcd for C30H32N2O4S [M+H]+ 517.66, observed 517.1.

Workup

  1. customquenched with an ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9dcd164b80314b7bb5c5b4cafe15e353
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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