Dichloromethane → HCID 89812998, compound

HRID 1481017Notes

Reaction equation

HRID 1481017 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](Br)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([O:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].[C:28]([Cu])#[N:29].C(Cl)Cl>CN(C=O)C>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([C:28]#[N:29])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([O:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 89813059HCID 89813059, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 89812998HCID 89812998, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Bromo-4-hydroxy-7-p-tolyloxy-isoquinoline-3-carboxylic acid butyl ester (130 mg, 0.30 mmol) and CuCN (54 mg, 0.61 mmol) were suspended in DMF (1.2 mL). The resulting mixture was heated to reflux for 40 minutes and then cooled to room temperature. The reaction crude was poured into CH2Cl2 (30 mL) and stirred vigorously for 10 minutes at room temperature. The resulting suspension was filtered through a pad of celite and the filtrate was washed with H2O and brine sequentially. The organic layer was dried over MgSO4, concentrated, and purified by flash chromatography (0-30% EtOAc/hexanes) to give the title compound in 65 mg. MS: (−) m/z 375.29 (M−1).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 40 minutes
  3. customThe reaction crude
  4. filtrationThe resulting suspension was filtered through a pad of celite
  5. washthe filtrate was washed with H2O and brine sequentially
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated
  8. custompurified by flash chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c31f28ea1f92475d9448ade54395c77b
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

Loading…