Potassium Carbonate → HCID 57507319, compound

HRID 556481Notes

Reaction equation

HRID 556481 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][CH2:9][NH:10][CH:11]([CH3:13])[CH3:12])([CH3:4])([CH3:3])[CH3:2].Br[C:16]1([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[NH:18][C:17]1=[O:26].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C(#N)C>[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][CH2:9][N:10]([C:16]1([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[NH:18][C:17]1=[O:26])[CH:11]([CH3:12])[CH3:13])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 16743802tert-Butyl {2-[(propan-2-yl)amino]ethyl}carbamateHCID 575072733-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

Product 1

HCID 57507319HCID 57507319, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (2-Isopropylamino-ethyl)-carbamic acid tert-butyl ester (100 mg, 0.5 mmol), rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (185 mg, 0.5 mmol) and K2CO3 (138 mg, 1 mmol) in DCM (1 mL) and acetonitrile (2 mL) was stirred at room temperature overnight. The mixture was concentrated and purified by column chromatography to give 180 mg rac-(2-{[6-Chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-isopropyl-amino}-ethyl)-carbamic acid tert-butyl ester. MS: [M+H]+=492

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-acd91964d2f145e08b5dee613e26cd14
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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