Chlorotrimethylsilane → HCID 91513171, compound

HRID 1627776Notes

Reaction equation

HRID 1627776 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][C:14]=1[CH3:22])=O.[C:23]([O:30][CH3:31])(=[O:29])[CH2:24][CH2:25][C:26]([CH3:28])=O.Cl[Si](C)(C)C>CN(C=O)C>[CH3:31][O:30][C:23](=[O:29])[CH2:24][C:25]1[C:11]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]=2[CH3:22])=[C:3]2[C:4]3[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=3[S:6][C:2]2=[N:1][C:26]=1[CH3:28]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 69354Methyl levulinateHCID 66603492HCID 66603492, compound

Product 1

HCID 91513171HCID 91513171, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure B from (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)(2-methyl-1H-indol-3-yl)methanone (0.310 g; 1 mmol), methyl levulinate (0.141 mL; 1.1 mmol), chlorotrimethylsilane (0.511 mL; 4 mmol) in DMF (4 mL) for 48 h. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (5-70%) in heptane furnished 0.233 g (57%) of the title compound as a yellow solid.

Workup

  1. customThis compound was prepared
  2. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (5-70%) in heptane

Sources & evidence

ORD record
ord-118104025e5749cba189ed09b1f23230
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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