2-Fluorobenzonitrile → 2-(3-(Bromomethyl)-6-fluoro-1H-indazol-1-yl)benzonitrile

HRID 1055413Notes

Reaction equation

HRID 1055413 reaction equation
[Br:1][CH2:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[C:14]#[N:15])[N:4]=1.[F:20]C1C=C2C(C(C)=NN2)=CC=1.FC1C=CC=CC=1C#N>O>[Br:1][CH2:2][C:3]1[C:11]2[C:6](=[CH:7][C:8]([F:20])=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[C:14]#[N:15])[N:4]=1

Participants

5

Reactant 3

HCID 678552-FluorobenzonitrileHCID 900376452-(3-Bromomethyl-indazol-1-yl)-benzonitrileHCID 1784343226-fluoro-3-methyl-1H-indazole

Product 1

HCID 900364802-(3-(Bromomethyl)-6-fluoro-1H-indazol-1-yl)benzonitrileYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a similar manner to that described for the preparation of 2-(3-(bromomethyl)-1H-indazol-1-yl)benzonitrile except in Step 1 the mixture was diluted with H2O and in Step 2 the mixture was heated at reflux overnight, 6-fluoro-3-methyl-1H-indazole (2 g, 13.3 mmol) and 2-fluorobenzonitrile (1.73 mL, 16 mmol) were converted to the title compound (800 mg, 61%) as an off white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight

Sources & evidence

ORD record
ord-344dba2aa7104388a453ca4d2ab29288
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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