Dimethylformamide → HCID 21082195, compound

HRID 346862Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:34])=[C:11]([CH2:13][N:14]3[C:22]4[C:17](=[CH:18][C:19]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:20][CH:21]=4)[CH:16]=[C:15]3[CH3:33])[N:12]=2)[CH:5]=[CH:6][CH:7]=1.CN([CH:38]=[O:39])C.O=P(Cl)(Cl)Cl>ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:34])=[C:11]([CH2:13][N:14]3[C:22]4[C:17](=[CH:18][C:19]([C:23]([OH:32])([C:24]([F:26])([F:27])[F:25])[C:28]([F:29])([F:30])[F:31])=[CH:20][CH:21]=4)[C:16]([CH:38]=[O:39])=[C:15]3[CH3:33])[N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 200 mg (0.4 mmol) of 2-{1-[2-(3-chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-2-methyl-1H-indol-5-yl}-1,1,1,3,3,3-hexafluoro-propan-2-ol (example 12) in 2 mL of dichloroethane was treated with 0.06 mL (0.8 mmol) of DMF and cooled to 0° C. After addition of 0.04 mL (0.44 mmol) of POCl3 the mixture was allowed to reach RT and stirred for an additional hour. Distribution of the mixture between Et2O and H2O, drying of the combined organic phases over Na2SO4 and column chromatography on silica gel with n-heptane/EtOAc 1:2 yielded 110 mg (52%) of 1-[2-(3-chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-1H-indole-3-carbaldehyde, light brown solid, MS: 531 (MH+).

Workup

customto reach RT
dry with materialDistribution of the mixture between Et2O and H2O, drying of the combined organic phases over Na2SO4 and column chromatography on silica gel with n-heptane/EtOAc 1:2

Sources & evidence

ORD record: ord-fd4ce9770e184784aff745eb5b4465c8
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173048B2

Reaction notes

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