Tributylphosphine → HCID 69142466, compound

HRID 860692Notes

Reaction equation

HRID 860692 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 87.2%

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 (106 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 (150 mg).

Workup

  1. additionfilled with nitrogen for 3 times

Sources & evidence

ORD record
ord-d31baa45e48d429dae12b75faed074f0
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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