Triethylamine → (4Z)-6-bromo-4-[(2,3-dihydro-1H-indol-5-ylamino)methylidene]isoquinoline-1,3-dione

HRID 2236677Notes

Reaction equation

HRID 2236677 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]2=[CH:14]OC.[NH:17]1[C:25]2[C:20](=[CH:21][C:22]([NH2:26])=[CH:23][CH:24]=2)[CH2:19][CH2:18]1.CCN(CC)CC>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:26][C:22]1[CH:21]=[C:20]2[C:25](=[CH:24][CH:23]=1)[NH:17][CH2:18][CH2:19]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27353522,3-Dihydro-1H-indol-5-amineHCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dione

Product 1

HCID 178518251(4Z)-6-bromo-4-[(2,3-dihydro-1H-indol-5-ylamino)methylidene]isoquinoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione (250 mg, 0.89 mmol), 2,3-dihydro-1H-indol-5-ylamine×2HCl (184 mg, 0.89 mmol) and Et3N (0.37 mL, 2.67 mmol) in N,N-dimethylformamide (DMF) (10 mL) is stirred for 4 days. The reaction mixture is concentrated in vacuo and the residue is triturated in H2O for 24 hours. The precipitate is filtered, washed with H2O and dried in vacuo to give 370 mg of the title compound as a brown solid. HRMS (ESI) m/z calcd for C18H14BrN3O2 (M+H)+1 384.03422. found: 384.03553. The compound is contains 29% of 4-(5-amino-2,3-dihydro-indol-1-ylmethylene)-6-bromo-4H-isoquinoline-1,3-dione.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe residue is triturated in H2O for 24 hours
  3. filtrationThe precipitate is filtered
  4. washwashed with H2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-f383c3e87b184791a67a2535d81c6360
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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