Boron tribromide → 2-{4-[2-cyclopentyl-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-benzenesulfonyl}-ethanol

HRID 1515809Notes

Reaction equation

HRID 1515809 reaction equation
[CH:1]1([CH2:6][CH:7]([C:22]2[NH:31][C:25]3=[N:26][CH:27]=[C:28]([F:30])[CH:29]=[C:24]3[CH:23]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH2:17][CH2:18][O:19]CC)(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>ClCCl>[CH:1]1([CH2:6][CH:7]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([CH2:17][CH2:18][OH:19])(=[O:16])=[O:15])=[CH:12][CH:13]=2)[C:22]2[NH:31][C:25]3=[N:26][CH:27]=[C:28]([F:30])[CH:29]=[C:24]3[CH:23]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 672289932-{2-cyclopentyl-1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-ethyl}-5-fluoro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 532520282-{4-[2-cyclopentyl-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-benzenesulfonyl}-ethanolYield 20.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-{2-cyclopentyl-1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-ethyl}-5-fluoro-1H-pyrrolo[2,3-b]pyridine (210 mg, 0.47 mmol) in dichloromethane (10 mL) at 0° C. was added a solution of boron tribromide (0.22 ml, 2.36 mmol) in dichloromethane (10 ml). The mixture was stirred at 0° C. for 1 h. The reaction was quenched with a saturated aqueous sodium bicarbonate solution (20 mL). The mixture was extracted with dichloromethane (2×50 mL), washed with a saturated aqueous sodium bicarbonate solution (3×20 mL) and brine (3×20 mL), 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 (2-{4-[2-cyclopentyl-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-benzenesulfonyl}-ethanol (40 mg, 20%) as a white solid: LC/MS m/e calcd for C22H25FN2O3S [M+H]+ 417.52, observed 417.0; 1H NMR (400 MHz, CD3OD) δ ppm 7.98 (t, J=2.3 Hz, 1H), 7.83-7.88 (m, J=8.3 Hz, 2H), 7.56-7.65 (m, 3H), 6.38 (s, 1H), 4.89-4.99 (m, 1H), 4.68-4.84 (m, 1H), 4.59 (br. s., 1H), 4.29 (t, J=8.0 Hz, 1H), 3.82 (t, J=6.2 Hz, 2H), 3.37 (t, J=6.2 Hz, 2H), 2.22-2.30 (m, 1H), 2.05-2.13 (m, 1H), 1.58-1.85 (m, 4H), 1.42-1.54 (m, 2H), 1.13-1.34 (m, 3H).

Workup

  1. customThe reaction was quenched with a saturated aqueous sodium bicarbonate solution (20 mL)
  2. extractionThe mixture was extracted with dichloromethane (2×50 mL)
  3. washwashed with a saturated aqueous sodium bicarbonate solution (3×20 mL) and brine (3×20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification

Sources & evidence

ORD record
ord-46a33ae17f194e1893c5a6ff137819ac
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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