Lithium Hexamethyldisilazide → HCID 66764885, compound

HRID 1466793Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH3:21])[CH:5]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[CH2:34][C:35]1[CH:36]=[N:37][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:39][CH:40]=1>CN(C=O)C.C1COCC1>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[N:13]([CH2:34][C:35]3[CH:36]=[N:37][C:38]([C:41]([F:44])([F:42])[F:43])=[CH:39][CH:40]=3)[C:12]=2[CH3:21])[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester (0.050 g, 0.15 mmol) was dissolved in DMF:THF (1:1, 4 mL) and cooled to 0° C. Lithium bis(trimethylsilyl)amide solution (0.375 mL, 0.375 mmol, 1.0M in hexanes) was added. 3-(Chloromethyl)-6-(trifluoromethyl)pyridine (0.044 g, 0.225 mmol) was added and the reaction was allowed to warm to room temperature. After 20 minutes the reaction was heated to 50° C. for 1 hour and then submitted to aqueous workup to provide the title compound.

Workup

temperatureto warm to room temperature
temperatureAfter 20 minutes the reaction was heated to 50° C. for 1 hour

Sources & evidence

ORD record: ord-4efba11aa83c4620b77c3099972254c6
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000025B2

Reaction notes

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