HCID 67227846, compound → HCID 67229003, compound

HRID 1515800Notes

Reaction equation

HRID 1515800 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[C:19]([C:26]2[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[CH:28][CH:27]=2)=[CH:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:35]([Mg]Cl)([CH3:37])[CH3:36]>O1CCCC1>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[C:19]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([OH:34])([CH:35]([CH3:37])[CH3:36])[CH3:33])=[CH:30][CH:31]=2)=[CH:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 67227846HCID 67227846, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 67229003HCID 67229003, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1-{4-[1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-ethanone (prepared as in Example 64, 450 mg, 0.95 mmol) in dry tetrahydrofuran (20 mL) at 0° C. was added isopropylmagnesium chloride solution in tetrahydrofuran (2 M, 1.05 mL, 2.1 mmol) dropwise. After stirring at 0° C. for 3 h, the reaction was quenched with a saturated aqueous ammonium chloride solution (20 mL). The mixture was extracted with ethyl acetate (2×50 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 50% ethyl acetate/hexanes) afforded 2-{4-[1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-3-methyl-butan-2-ol (90 mg, 20%) as a white solid: LC/MS m/e calcd for C31H34N2O3S [M+H]+ 515.69, observed 515.2.

Workup

  1. customthe reaction was quenched with a saturated aqueous ammonium chloride solution (20 mL)
  2. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-429b90ba1b7b4c69a18dd0dbaa010f63
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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