1,2-Dichloroethane → 4-Nitrophenyl 7-(5-fluoro-2-methylphenyl)isoquinolin-3-ylcarbamate

HRID 468753Notes

Reaction equation

HRID 468753 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:19])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH2:18])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)[CH:7]=1.ClCCCl.C(N(CC)CC)C.Cl[C:32]([O:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)=[O:33].N1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:19])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH:18][C:32](=[O:33])[O:34][C:35]4[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=4)[N:14]=[CH:15]3)=[CH:10][CH:9]=2)[CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 1049PyridineHCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformate2×HCID 574102447-(5-Fluoro-2-methylphenyl)isoquinolin-3-amine

Product 1

HCID 679748684-Nitrophenyl 7-(5-fluoro-2-methylphenyl)isoquinolin-3-ylcarbamateYield 125.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 7-(5-fluoro-2-methylphenyl)isoquinolin-3-amine (0.5145 g, 2.039 mmol) in 1,2-dichloroethane (10 mL, 100 mmol) was added triethylamine (0.35 mL, 2.5 mmol) and p-nitrophenyl chloroformate (0.452 g, 2.24 mmol). The reaction mixture was stirred at room temperature for 16 hours and then pyridine (0.50 mL, 6.2 mmol) and p-nitrophenyl chloroformate (0.452 g, 2.24 mmol) were added. After an additional 2 hours, the reaction mixture was diluted with dichloromethane, washed with saturated aqueous NaHCO3, dried over MgSO4, and evaporated in vacuo. 1.069 g of 4-nitrophenyl 7-(5-fluoro-2-methylphenyl)isoquinolin-3-ylcarbamate was obtained, and carried forward without purification. LCMS (ESI): M+H=poor ionization.

Workup

  1. waitAfter an additional 2 hours
  2. washwashed with saturated aqueous NaHCO3
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-c5a904a911544ad2bfe88ed90f96ea20
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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