Dichloromethane → HCID 19595317, compound

HRID 612473Notes

Reaction equation

HRID 612473 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12]C)=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([NH:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[CH2:7]2.ClCCl.B(Br)(Br)[Br:25]>CO>[BrH:25].[F:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([NH:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[CH2:7]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 19595309HCID 19595309, compound

Product 1

HCID 19595317HCID 19595317, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (5-fluoro-8-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)-pyridin-4-yl-amine (4.82 g) and dichloromethane (100 ml) at -78° C., boron tribromide (5.5 ml) was added, with stirring. The reaction mixture was warmed to ambient temperature, stirred for 3 hrs, and methanol (100 ml) was added. The mixture was stirred for 1 hr and concentrated in vacuo. The residue was recrystallized from 2-propanol to yield 4.45 g (74%) of product, mp 266° C.

Workup

  1. stirringstirred for 3 hrs
  2. stirringThe mixture was stirred for 1 hr
  3. concentrationconcentrated in vacuo
  4. customThe residue was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-b6ac16d2518e4dce8e54dcebdd854ebd
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

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