Triethylamine → HCID 178455416, compound

HRID 2069786Notes

Reaction equation

HRID 2069786 reaction equation
[Br:1][C:2]1[C:3]([C:24]([CH3:32])([CH3:31])[O:25][SiH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[C:4]([N:8]2[CH:17](O)[CH2:16][C:15]3[C:10](=[CH:11][C:12]([C:19]4([CH3:22])[CH2:21][CH2:20]4)=[CH:13][CH:14]=3)[C:9]2=[O:23])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl>[Br:1][C:2]1[C:3]([C:24]([CH3:32])([CH3:31])[O:25][SiH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[C:4]([N:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][C:12]([C:19]4([CH3:22])[CH2:20][CH2:21]4)=[CH:13][CH:14]=3)[C:9]2=[O:23])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178455417HCID 178455417, compound

Product 1

HCID 178455416HCID 178455416, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[3-Bromo-2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-3-hydroxy-7-(1-methyl-cyclopropyl)-3,4-dihydro-2H-isoquinolin-1-one (1.134 g, 2.2 mmol) was dissolved in 13 ml dichloromethane at room temperature; triethylamine (1.31 ml, 9.44 mmol) followed by addition of methanesulfonyl chloride (0.478 g, 4.171 mmol) were added. It was stirred for 1.5 hours at room temperature but it's already done in 10 minutes according to LCMS. The reaction mixture was extracted with dichloromethane/water; organic phase was washed with brine; dried over sodium sulfate; filtered; concentrated to give 2-[3-Bromo-2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-7-(1-methyl-cyclopropyl)-2H-isoquinolin-1-one (1.094 g, 2.2 mmol) MS (ESI) 520.0 (M+Na+)

Workup

  1. additionwere added
  2. waitit's already done in 10 minutes
  3. extractionThe reaction mixture was extracted with dichloromethane/water
  4. washorganic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-139c36bbf6f44ec9b89b41f24b13a1fd
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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