Triethylamine → HCID 178455416, compound

HRID 41913Notes

Reaction equation

HRID 41913 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-c7889a6f73e04808997cd873ea1cd397
Source dataset
uspto-grants-2013_09
Patent number
US08536166B2

Reaction notes

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