Chlorotrimethylsilane → HCID 66597328, compound

HRID 1627775Notes

Reaction equation

HRID 1627775 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[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)=O.[C:24]([O:31][CH3:32])(=[O:30])[CH2:25][CH2:26][C:27]([CH3:29])=O.Cl[Si](C)(C)C>CN(C=O)C>[CH3:32][O:31][C:24](=[O:30])[CH2:25][C:26]1[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)=[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:27]=1[CH3:29]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 69354Methyl levulinateHCID 66603635HCID 66603635, compound

Product 1

HCID 66597328HCID 66597328, compoundYield 78.1%

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)(4-trifluoromethoxyphenyl)methanone (0.341 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 (5-40%) in heptane furnished 0.340 g (78%) 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 (5-40%) in heptane

Sources & evidence

ORD record
ord-30926f7ef7a54718887d90faa9ce53a3
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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