Tributylphosphine → HCID 69142466, compound

HRID 854577Notes

Reaction equation

HRID 854577 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH3:16])([CH3:4])([CH3:3])[CH3:2].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[N:30]=[CH:29][C:28]([C:31]2[S:32][C:33]([CH3:39])=[C:34]([CH2:36][CH2:37]O)[N:35]=2)=[CH:27][CH:26]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:37][CH2:36][C:34]2[N:35]=[C:31]([C:28]3[CH:29]=[N:30][C:25]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[F:18])=[CH:26][CH:27]=3)[S:32][C:33]=2[CH3:39])=[CH:11][C:10]=1[CH3:16])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 69139516HCID 69139516, compoundHCID 69141617HCID 69141617, compound

Product 1

HCID 69142466HCID 69142466, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-(4-Hydroxy-2-methyl-phenyl)-propionic acid tert-butyl ester (120 mg, 0.5 mmol) and 2-{2-[6-(2-Fluoro-phenyl)-pyridin-3-yl]-5-methyl-thiazol-4-yl}-ethanol (101 mg, 0.323 mmol) in toluene (3.0 mL) is degassed and filled with nitrogen for 3 times. Tributylphosphine (0.124 mL, 0.5 mmol) is added to the reaction mixture under nitrogen at 0° C., followed by addition of of 1,1′-(azodicarbonyl)-dipiperidine (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 gave the title compound (130 mg).

Workup

  1. additionfilled with nitrogen for 3 times

Sources & evidence

ORD record
ord-7e22afbfbafe4f229ae39197f4a6006e
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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