Chlorotrimethylsilane → HCID 24956864, compound

HRID 1095602Notes

Reaction equation

HRID 1095602 reaction equation
[CH3:1][N:2]([CH3:31])[C:3]1([C:26]2[S:27][CH:28]=[CH:29][CH:30]=2)[CH2:8][CH2:7][CH:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:5][CH2:4]1.[Si]([Cl:36])(C)(C)C>C(OCC)(=O)C>[ClH:36].[CH3:31][N:2]([CH3:1])[C:3]1([C:26]2[S:27][CH:28]=[CH:29][CH:30]=2)[CH2:4][CH2:5][CH:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 24956865HCID 24956865, compound

Product 1

HCID 24956864HCID 24956864, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N,N-dimethyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)-1-(thiophen-2-yl)cyclohexanamine (more polar diastereoisomer) (43 mg, 0.1 mmol) was dissolved in ethyl acetate (20 ml). Me3SiCl (19 μl, 0.15 mmol) was then added dropwise at RT and the mixture was stirred for 1 h. A white precipitate precipitated out. The precipitate was filtered off with suction, washed with ethyl acetate (2×5 ml) and then dried. Example 304 (40 mg, m.p. 188-191° C., yield 87%) was a white solid.

Workup

  1. customA white precipitate precipitated out
  2. filtrationThe precipitate was filtered off with suction
  3. washwashed with ethyl acetate (2×5 ml)
  4. customdried

Sources & evidence

ORD record
ord-aa5c27e2688049258f37c0e742d31ea5
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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