(Trifluoromethyl)trimethylsilane → HCID 22676779, compound

HRID 1006281Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)[C:10]=2[CH:29]=[O:30])=[CH:5][CH:4]=1.[Si]([C:35]([F:38])([F:37])[F:36])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[F:36][C:35]([F:38])([F:37])[CH:29]([C:10]1[N:11]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=2)[C:12]2[C:17]([C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2)[OH:30]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-(4-methoxyphenyl)-1-{[3-(trifluoromethyl)phenyl]methyl}indole-2-carbaldehyde (Example 218, 200 mg, 0.49 mmol) in tetrahydrofuran (5 mL) was added a 0.5 M solution of TMSCF3 in tetrahydrofuran (4.9 mL, 2.4 mmol). The resulting solution was cooled to 0° C. and a 1.0 M solution of TBAF in tetrahydrofuran (0.10 mL, 0.10 mmol) was added. The mixture was stirred for 10 min at 0° C. and then let warm to RT and quenched by the addition of water. The resulting mixture was extracted with tetrahydrofuran, adsorbed onto silica, and purified by flash chromatography on silica in 4:1 hexane:ethyl acetate (v/v) to yield 49 mg (21%) of an orange solid. 1H NMR (300 MHz, DMSO-d6) δ 7.60-7.26 (m, 6H), 7.22-7.01 (m, 6H), 5.81 (s, 2H), 3.83 (s, 3H); mass spectroscopy gave MH+=480.2 (calc'd exact mass for C25H19F3NO2=479.13).

Workup

temperaturelet warm to RT
customquenched by the addition of water
extractionThe resulting mixture was extracted with tetrahydrofuran
custompurified by flash chromatography on silica in 4:1 hexane

Sources & evidence

ORD record: ord-03b5349e0c5a4aceaf083bf4ad7179cc
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06787651B2

Reaction notes

Loading…