Tributylphosphine → HCID 69356322, compound

HRID 860659Notes

Reaction equation

HRID 860659 reaction equation
[SH:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[C:4]([CH3:13])[CH:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=1[CH2:22][CH2:23][C:24]1[N:25]=[C:26]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)[S:27][C:28]=1[CH:29](O)[CH3:30].[CH2:42](P(CCCC)CCCC)[CH2:43]CC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[CH2:42]([O:9][C:8](=[O:10])[CH2:7][O:6][C:5]1[CH:11]=[CH:12][C:2]([S:1][CH:29]([C:28]2[S:27][C:26]([C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=3)=[N:25][C:24]=2[CH2:23][CH2:22][C:16]2[C:17]([F:21])=[CH:18][CH:19]=[CH:20][C:15]=2[Cl:14])[CH3:30])=[CH:3][C:4]=1[CH3:13])[CH3:43]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 21908086HCID 21908086, compoundHCID 58765839HCID 58765839, compound

Product 1

HCID 69356322HCID 69356322, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (4-Mercapto-2-methyl-phenoxy)-acetic acid (158 mg, 0.7 mmol) and 1-[4-[2-(2-Chloro-6-fluoro-phenyl)-ethyl]-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethanol (200 mg, 0.465 mmol) in toluene (3.0 mL) is degassed and filled with nitrogen for 3 times. Tributylphosphine (0.174 mL, 0.7 mmol) is added to the reaction mixture under nitrogen at 0° C., followed by addition of of 1,1′-(azodicarbonyl)-dipiperidine (177 mg, 0.7 mmol). The reaction mixture is allowed to warm to room temperature and stirred overnight, the mixture is loaded on silica gel column. Chromatography gave the title compound (160 mg).

Workup

  1. additionfilled with nitrogen for 3 times

Sources & evidence

ORD record
ord-9c1d234cd4584be79983f15d0228bf89
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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