Tetrahydrofuran → HCID 67228043, compound

HRID 1515797Notes

Reaction equation

HRID 1515797 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:17]2[N:25]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH:18]=2)=[CH:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1.[CH2:36]([Mg]Br)[CH3:37].O1CC[CH2:42][CH2:41]1>>[C:29]1([S:26]([N:25]2[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH:18]=[C:17]2[C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:2])([CH2:36][CH3:37])[CH2:41][CH3:42])=[CH:5][CH:6]=2)=[CH:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)(=[O:27])=[O:28])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 67228155HCID 67228155, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 67228043HCID 67228043, compoundYield 63%

Conditions

Temperature
0 °C

Procedure

To a solution of 4-[1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-benzoic acid methyl ester (330 mg, 0.68 mmol) in dry tetrahydrofuran (20 mL) at 0° C. was added an ethylmagnesium bromide solution in tetrahydrofuran (3.0 M, 1.14 mL, 3.4 mmol) dropwise. After stirring at 0° C. for 1 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, 25% ethyl acetate/hexanes) afforded 3-{4-[1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-pentan-3-ol (220 mg, 63%) 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, 25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b7e8ffa50c944d9d8fd68a15506d676c
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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