Triphenylphosphine → N-(2-bromo-pyridin-4-ylmethyl)-2-chloro-N-isobutyl-benzenesulfonamide

HRID 1665072Notes

Reaction equation

HRID 1665072 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:22]=[C:21]([CH2:23]O)[CH:20]=[CH:19][N:18]=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:22]=[C:21]([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])[CH:20]=[CH:19][N:18]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 84693762-chloro-N-isobutyl-benzenesulfonamideHCID 14512957(2-Bromopyridin-4-yl)methanol

Product 1

HCID 86629146N-(2-bromo-pyridin-4-ylmethyl)-2-chloro-N-isobutyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to example 45, step 1, 2-chloro-N-isobutyl-benzenesulfonamide (example 42, step 1) was reacted with (2-bromo-pyridin-4-yl)-methanol (CAS [118289-16-0]), triphenylphosphine and diethyl azodicarboxylate in tetrahydrofuran to give N-(2-bromo-pyridin-4-ylmethyl)-2-chloro-N-isobutyl-benzenesulfonamide as a colorless oil. MS: 417.2 ([M+H]+)

Sources & evidence

ORD record
ord-d971fedbdf8840f98404fa725886d035
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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