4-(2-Bromo-ethyl)-2,5-diphenyl-oxazole → 2-{1-[2-(2,5-diphenyl-oxazol-4-yl)-ethyl]-2-methyl-2,3-dihydro-1H-indol-5-yl}-1,1,1,3,3,3-hexafluoro-propan-2-ol

HRID 346851Notes

Reaction equation

HRID 346851 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]([CH3:18])[CH2:12]2)([OH:8])[C:4]([F:7])([F:6])[F:5].Br[CH2:22][CH2:23][C:24]1[N:25]=[C:26]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:27][C:28]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[C:35]1([C:26]2[O:27][C:28]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[C:24]([CH2:23][CH2:22][N:14]3[C:15]4[C:11](=[CH:10][C:9]([C:3]([OH:8])([C:2]([F:1])([F:19])[F:20])[C:4]([F:7])([F:6])[F:5])=[CH:17][CH:16]=4)[CH2:12][CH:13]3[CH3:18])[N:25]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 210822174-(2-Bromo-ethyl)-2,5-diphenyl-oxazoleHCID 233461261,1,1,3,3,3-hexafluoro-2-(2-methyl-2,3-dihydro-1H-indol-5-yl)-propan-2-ol

Product 1

HCID 115195942-{1-[2-(2,5-diphenyl-oxazol-4-yl)-ethyl]-2-methyl-2,3-dihydro-1H-indol-5-yl}-1,1,1,3,3,3-hexafluoro-propan-2-olYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 100 mg (0.33 mmol) of 1,1,1,3,3,3-hexafluoro-2-(2-methyl-2,3-dihydro-1H-indol-5-yl)-propan-2-ol (example 51.1) and 4-(2-bromo-ethyl)-2,5-diphenyl-oxazole in 0.5 mL of DMF was stirred at 80° C. overnight. Distribution of the mixture between a saturated aqueous solution of NH4Cl and Et2O, drying of the combined organic phases over Na2SO4 and column chromatography on silica gel with n-heptane/EtOAc 4:1 yielded 39 mg (21%) of 2-{1-[2-(2,5-diphenyl-oxazol-4-yl)-ethyl]-2-methyl-2,3-dihydro-1H-indol-5-yl}-1,1,1,3,3,3-hexafluoro-propan-2-ol, light yellow gum, MS: 547 (MH+).

Workup

  1. dry with materialDistribution of the mixture between a saturated aqueous solution of NH4Cl and Et2O, drying of the combined organic phases over Na2SO4 and column chromatography on silica gel with n-heptane/EtOAc 4:1

Sources & evidence

ORD record
ord-d77fb08a46f04db2ae474028d181fc1e
Source dataset
uspto-grants-2007_02
Patent number
US07173048B2

Reaction notes

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