Sodium Hydroxide → 1-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-ol

HRID 1515631Notes

Reaction equation

HRID 1515631 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([O:19]C)[CH:18]=[C:13]3[CH:12]=[C:11]2[C:21]([C:28]2[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O: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.B(Br)(Br)Br.[OH-].[Na+]>ClCCl>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([OH:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:21]([C:28]2[CH:29]=[CH:30][C:31]([S:34]([CH3:37])(=[O:35])=[O:36])=[CH:32][CH:33]=2)=[CH:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 672286121-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-methoxy-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 672285961-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-olYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-methoxy-1H-pyrrolo[2,3-b]pyridine (prepared as in Example 12, 950 mg, 1.77 mmol) in dry dichloromethane (30 mL) at −78° C. was added a solution of boron tribromide (1.7 mL, 17.7 mmol) in dry dichloromethane (10 mL). The mixture was then warmed to room temperature and stirred for 1 h. The solution was poured into ice-water and neutralized with a 2.5M aqueous sodium hydroxide solution (pH ˜6). The mixture was extracted with ethyl acetate (2×250 mL), washed with brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to give 1-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-ol (925 mg, 100%) as a light yellow solid which was used in the next step without further purification: LC/MS m/e calcd for C27H26N2O5S2 [M+H]+ 523.65, observed 523.1.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×250 mL)
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-357431153c714773a1c2a14c357dfb20
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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