Tributylphosphine → (6-{2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propoxy}-benzo[b]thiophen-3-yl)-acetic acid ethyl ester

HRID 490767Notes

Reaction equation

HRID 490767 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH:17]([CH3:20])[CH2:18][OH:19].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[CH2:52]([O:54][C:55](=[O:67])[CH2:56][C:57]1[C:58]2[CH:65]=[CH:64][C:63](O)=[CH:62][C:59]=2[S:60][CH:61]=1)[CH3:53]>C1(C)C=CC=CC=1>[CH2:52]([O:54][C:55](=[O:67])[CH2:56][C:57]1[C:58]2[CH:65]=[CH:64][C:63]([O:19][CH2:18][CH:17]([C:3]3[N:4]=[C:5]([C:7]4[CH:8]=[CH:9][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:12]=4)[S:6][C:2]=3[CH3:1])[CH3:20])=[CH:62][C:59]=2[S:60][CH:61]=1)[CH3:53]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 57431998(6-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl esterHCID 587656942-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propan-1-ol

Product 1

HCID 69055659(6-{2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propoxy}-benzo[b]thiophen-3-yl)-acetic acid ethyl esterYield 96.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-[5-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propan-1-ol (226 mg, 0.75 mmol) in toluene (4.0 mL) is degassed and filled with nitrogen for 3 times. O this solution is added 1,1′-(azodicarbonyl)-dipiperidine (190 mg, 0.75 and mmol) and tributylphosphine (0.186 mL, 0.75 mmol) under nitrogen at 0° C., followed by addition of (6-hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester (120 mg, 0.5 mmol). The reaction mixture is allowed to warm to room temperature and stirred overnight, the mixture is loaded on silica gel column. Chromatography yields the title compound (250 mg).

Workup

  1. additionfilled with nitrogen for 3 times

Sources & evidence

ORD record
ord-195406ffd8b4459ebff55d120b140062
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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