Triphenylphosphine → methyl 3-(4-{(4-{[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]methoxy}benzyl)[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

HRID 508039Notes

Reaction equation

HRID 508039 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=1)(=[O:12])=[O:11])([O-:3])=[O:2].[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[N:37]([CH3:38])[N:36]=[CH:35][C:34]=2[CH2:39][O:40][C:41]2[CH:46]=[CH:45][C:44]([CH2:47]O)=[CH:43][CH:42]=2)=[CH:29][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl>[F:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]2[N:37]([CH3:38])[N:36]=[CH:35][C:34]=2[CH2:39][O:40][C:41]2[CH:42]=[CH:43][C:44]([CH2:47][N:13]([S:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=3)=[CH:45][CH:46]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23157467Methyl 3-(4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoateHCID 23157546(4-{[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]methoxy}phenyl)methanol

Product 1

HCID 23157545methyl 3-(4-{(4-{[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]methoxy}benzyl)[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-(4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (182 mg, 0.5 mmol), (4-{[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]methoxy}phenyl)methanol (156 mg, 0.5 mmol) and triphenylphosphine (262 mg, 1.0 mmol) in dichloromethane (5 mL) was added diethyl azodicarboxylate (40% toluene solution, 435 mg, 1.0 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was purified by silica gel column chromatography (10%-80% ethyl acetate/hexane) to give a yellow oil containing the title compound.

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (10%-80% ethyl acetate/hexane)
  2. customto give a yellow oil

Sources & evidence

ORD record
ord-f90ccc57474d4b3e99741d436c995394
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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