Triethylamine → HCID 178455416, compound

HRID 2188754Notes

Reaction equation

HRID 2188754 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-ad78a6e9480c479786d4c3316ed07114
Source dataset
uspto-grants-2012_12
Patent number
US08324211B2

Reaction notes

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