HCID 21082219, compound → HCID 21082154, compound

HRID 346870Notes

Reaction equation

HRID 346870 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:15][N:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25]([OH:34])([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])=[CH:22][CH:23]=2)[CH:18]=[C:17]1[CH3:35].[CH3:36][Mg]Br>C1COCC1.C(OCC)C>[F:29][C:26]([F:27])([F:28])[C:25]([C:21]1[CH:20]=[C:19]2[C:24](=[CH:23][CH:22]=1)[N:16]([CH2:15][C:3]1[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]([CH:11]([OH:12])[CH3:36])=[CH:13][CH:14]=3)[O:6][C:2]=1[CH3:1])[C:17]([CH3:35])=[CH:18]2)([OH:34])[C:30]([F:33])([F:32])[F:31]

Participants

5

Reactant 2

HCID 21082219HCID 21082219, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 21082154HCID 21082154, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 50 mg (0.1 mmol) of 4-{5-methyl-4-[2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-indol-1-ylmethyl]-oxazol-2-yl}-benzaldehyde in 1 ml of THF was cooled to 0° C. and treated with 0.13 ml (0.4 mmol) of a 3M methylmagnesium bromide solution in diethylether. The mixture was stirred and allowed to reach RT within 1 hr. Distribution of the crude between a saturated aqueous solution of NH4Cl and EtOAc, drying of the combined organic phases over Na2SO4, evaporation of the solvent, and chromatography on silica gel with heptane/EtOAc 4:1 gave 44 mg (85%) of 1,1,1,3,3,3-hexafluoro-2-(1-{2-[4-(1-hydroxy-ethyl)-phenyl]-5-methyl-oxazol-4-ylmethyl}-2-methyl-1H-indol-5-yl)-propan-2-ol, off-white solid, MS: 513 (MH+).

Workup

  1. dry with materialDistribution of the crude between a saturated aqueous solution of NH4Cl and EtOAc, drying of the combined organic phases over Na2SO4, evaporation of the solvent, and chromatography on silica gel with heptane/EtOAc 4:1

Sources & evidence

ORD record
ord-45bb93fa7ec8438e9362ea0e56f7b654
Source dataset
uspto-grants-2007_02
Patent number
US07173048B2

Reaction notes

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