Triethylamine → HCID 178455415, compound

HRID 2245729Notes

Reaction equation

HRID 2245729 reaction equation
[Br:1][C:2]1[C:3]([C:23]([CH3:31])([CH3:30])[O:24][SiH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[C:4]([N:8]2[CH:17](O)[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([CH:19]4[CH2:21][CH2:20]4)[CH:14]=3)[C:9]2=[O:22])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]([C:23]([CH3:31])([CH3:30])[O:24][SiH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[C:4]([N:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([CH:19]4[CH2:20][CH2:21]4)[CH:14]=3)[C:9]2=[O:22])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178455418HCID 178455418, compound

Product 1

HCID 178455415HCID 178455415, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a rapidly stirred solution of 2-[3-bromo-2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-6-cyclopropyl-3-hydroxy-3,4-dihydro-2H-isoquinolin-1-one (3.52 g, 7.00 mmol) and triethylamine (4.0 mL, 29 mmol) in 50 mL of anhydrous CH2Cl2 was added 0.85 mL of methanesulfonyl chloride. Purged the flask with nitrogen and stirred at room temperature overnight. Added 25 mL of CH2Cl2 and 50 mL of water and separated phases. Washed the organic phase with 50 ml brine. Dried the solution over MgSO4 and concentrated in vacuo. Purified the residue by flash chromatography (gradient elution, 0 to 50% EtOAc/hexane) to obtain 2-[3-Bromo-2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-6-cyclopropyl-2H-isoquinolin-1-one as an amber resin (2.90 g, 5.99 mmol). MS (ESI) 484, 486 (M+H)+.

Workup

  1. customPurged the flask with nitrogen
  2. additionAdded 25 mL of CH2Cl2 and 50 mL of water
  3. customseparated phases
  4. washWashed the organic phase with 50 ml brine
  5. dry with materialDried the solution over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurified the residue
  8. washby flash chromatography (gradient elution, 0 to 50% EtOAc/hexane)

Sources & evidence

ORD record
ord-790ef18bcf1149c6b16580746ec18f33
Source dataset
uspto-grants-2010_03
Patent number
US07683064B2

Reaction notes

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