Dichloromethane → HCID 89813257, compound

HRID 1481014Notes

Reaction equation

HRID 1481014 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:10]=2)[C:5](I)=[N:4][C:3]=1[C:24]([O:26][CH3:27])=[O:25].[C:28]([Cu])#[N:29].C(Cl)Cl>CN(C=O)C>[C:28]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([O:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[CH:7]=2)[C:2]([OH:1])=[C:3]([C:24]([O:26][CH3:27])=[O:25])[N:4]=1)#[N:29]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 89813064HCID 89813064, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 89813257HCID 89813257, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Methyl 4-hydroxy-1-iodo-7-(naphthalen-1-yloxy)isoquinoline-3-carboxylate (130 mg, 0.28 mmol) and CuCN (49 mg, 0.55 mmol) were suspended in DMF (1.1 mL). The resulting mixture was heated at 120° C. for 7 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 (0-50% EtOAc/hexanes) to give the title compound in 87 mg. MS: (−) m/z 369.31 (M−1).

Workup

  1. temperaturecooled to room temperature
  2. customThe reaction crude
  3. filtrationThe resulting suspension was filtered through a pad of celite
  4. washthe filtrate was washed with H2O and brine sequentially
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. custompurified by flash chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c90ac094d25f4649be032425b3ce4c8e
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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