Triphenylphosphine → N-(5-bromo-pyridin-2-ylmethyl)-2-chloro-N-isobutyl-benzenesulfonamide

HRID 1665067Notes

Reaction equation

HRID 1665067 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9].[Br:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:23]O)=[N:21][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Br:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:23][N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[S:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])(=[O:9])=[O:10])=[N:21][CH:22]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5200169(5-Bromopyridin-2-yl)methanolHCID 84693762-chloro-N-isobutyl-benzenesulfonamide

Product 1

HCID 67439287N-(5-bromo-pyridin-2-ylmethyl)-2-chloro-N-isobutyl-benzenesulfonamideYield 57.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-chloro-N-isobutyl-benzenesulfonamide (example 42, step 1, 110 mg) in tetrahydrofuran (2.5 mL) were added (5-bromo-pyridin-2-yl)-methanol (CAS [88139-91-7], 92 mg), triphenylphosphine (129 mg) and diethyl azodicarboxylate (88 mg). The mixture was stirred for 48 h at r.t. The solvent was evaporated under reduced pressure and the product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:0 to 0:1) to give N-(5-bromo-pyridin-2-ylmethyl)-2-chloro-N-isobutyl-benzenesulfonamide (106 mg) as a colorless oil. MS: 417.2 ([M+H]+)

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:0 to 0:1)

Sources & evidence

ORD record
ord-09facf3a089e4d3d98cf7ccecd01739e
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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