Azobisisobutyronitrile → 4-bromo-8-fluoroisoquinoline

HRID 1521569Notes

Reaction equation

HRID 1521569 reaction equation
CO[CH:3](OC)[CH2:4][N:5]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23])S(C1C=CC(C)=CC=1)(=O)=O.[Br:26]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:26][C:3]1[C:22]2[C:17](=[C:18]([F:23])[CH:19]=[CH:20][CH:21]=2)[CH:16]=[N:5][CH:4]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 89155471N-(2,2-Dimethoxyethyl)-N-[(2-fluorophenyl)methyl]-4-methylbenzenesulfonamide

Product 1

HCID 709768624-bromo-8-fluoroisoquinoline

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(2,2-dimethoxyethyl)-N-(2-fluorobenzyl)-4-methylbenzenesulfonamide (DD; 0.6 g, 0.0041 mol) in carbon tetrachloride (15 mL) was added N-bromosuccinimide (1.08 g, 0.00603 mol) followed by AIBN (0.06 g, 0.00041 mol) and heated for 3 h at 80° C. Then carbon tetrachloride was evaporated and the crude was purified by column chromatography to get the title compound. 1H NMR (400 MHz, CDCl3) δ 9.46 (1H, s), 8.80 (s, 1H), 7.97-7.95 (d, J=8.4 Hz, 1H), 7.79-7.74 (m, 1H), 7.35-7.31 (dd, J=8.0, 9.6 Hz, 1H).

Workup

  1. customThen carbon tetrachloride was evaporated
  2. customthe crude was purified by column chromatography

Sources & evidence

ORD record
ord-e6fb4360f7b14e019d9251e7a3f61b12
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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