Boron tribromide → 6-(adamantan-1-ylmethoxy)-5-cyclopropyl-N-((2-hydroxyethyl)sulfonyl)nicotinamide

HRID 1849696Notes

Reaction equation

HRID 1849696 reaction equation
[C:1]12([CH2:11][O:12][C:13]3[C:28]([CH:29]4[CH2:31][CH2:30]4)=[CH:27][C:16]([C:17]([NH:19][S:20]([CH2:23][CH2:24][O:25]C)(=[O:22])=[O:21])=[O:18])=[CH:15][N:14]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.B(Br)(Br)Br>ClCCl.C(OCC)(=O)C>[C:1]12([CH2:11][O:12][C:13]3[C:28]([CH:29]4[CH2:31][CH2:30]4)=[CH:27][C:16]([C:17]([NH:19][S:20]([CH2:23][CH2:24][OH:25])(=[O:22])=[O:21])=[O:18])=[CH:15][N:14]=3)[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 867035666-(adamantan-1-ylmethoxy)-5-cyclopropyl-N-((2-methoxyethyl)-sulfonyl)nicotinamide

Product 1

HCID 867035676-(adamantan-1-ylmethoxy)-5-cyclopropyl-N-((2-hydroxyethyl)sulfonyl)nicotinamideYield 98.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-(adamantan-1-ylmethoxy)-5-cyclopropyl-N-((2-methoxyethyl)-sulfonyl)nicotinamide (0.19 g, 0.42 mmol) in anhydrous dichloromethane (10 mL) at 0° C. was treated with boron tribromide (0.079 mL, 0.84 mmol) under nitrogen. The reaction mixture was stirred for 25 minutes and then diluted with ethyl acetate (50 mL). The mixture was washed with 1 M aqueous hydrochloric acid solution (2×30 mL), brine (30 mL); dried over anhydrous sodium sulfate; filtered and concentrated in vacuo to provide the title compound (0.18 g, quant.): 1H NMR (300 MHz, DMSO-d6) δ 11.91 (br s, 1H), 8.45 (d, J=2.3 Hz, 1H), 7.70 (d, J=2.3 Hz, 1H), 4.95 (br s, 1H), 3.93 (s, 2H), 3.80-3.73 (m, 2H), 3.65-3.58 (m, 2H), 2.07-1.98 (m, 1H), 1.98-1.90 (m, 3H), 1.73-1.57 (m, 12H), 0.98-0.90 (m, 2H), 0.76-0.70 (m, 2H); MS (ES+) m/z 435.2 (M+1).

Workup

  1. washThe mixture was washed with 1 M aqueous hydrochloric acid solution (2×30 mL), brine (30 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e269cd24cc0847758dd77657c9be835b
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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