Sodium Hydroxide → 3-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-propan-1-ol

HRID 1515696Notes

Reaction equation

HRID 1515696 reaction equation
[CH:1]1([CH2:6][CH:7]([C:18]2[NH:31][C:21]3=[N:22][CH:23]=[C:24]([CH2:26][CH2:27][CH2:28][O:29]C)[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.[OH-].[Na+]>ClCCl>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:31][C:21]3=[N:22][CH:23]=[C:24]([CH2:26][CH2:27][CH2:28][OH:29])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 53251247HCID 53251247, compound

Product 1

HCID 532512483-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-propan-1-olYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To stirred solution of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-(3-methoxy-propyl)-1H-pyrrolo[2,3-b]pyridine (prepared as in Example 44, 90 mg, 0.21 mmol) in dry dichloromethane (10 mL) was added a solution of boron tribromide (0.67 mL, 6.95 mmol) in dry dichloromethane (5 mL) at −78° C. The mixture was warmed to room temperature and stirred for 1 h. The mixture was poured into ice-water, neutralized with a 2.5 M aqueous sodium hydroxide solution (pH ˜6) and then extracted with ethyl acetate (2×250 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 3-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-propan-1-ol (20 mg, 23%) as a white solid: LC/MS m/e calcd for C24H30N2O3S [M+H]+ 427.58, observed 427.1; 1H NMR (400 MHz, CD3OD) δ ppm 8.35 (s, 1H), 8.14 (br. s., 1H), 7.90-7.95 (m, J=8.1 Hz, 2H), 7.60-7.65 (m, J=8.3 Hz, 2H), 6.67-6.72 (m, 1H), 4.37-4.46 (m, 1H), 3.62 (t, J=6.2 Hz, 2H), 3.11 (s, 3H), 2.92 (t, J=7.7 Hz, 2H), 2.26-2.35 (m, 1H), 2.14-2.23 (m, 1H), 1.83-1.96 (m, 3H), 1.64-1.81 (m, 4H), 1.47-1.58 (m, 2H), 1.20-1.33 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate (2×250 mL)
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification

Sources & evidence

ORD record
ord-87d2b808a4504e61b9a82702ce8dce3a
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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