Methyl 3-cyano-4-fluorobenzoate → Methyl 3-cyano-4-(3-(bromomethyl)-1H-indazol-1-yl)benzoate

HRID 1055418Notes

Reaction equation

HRID 1055418 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.CC1C2C(=CC=CC=2)NN=1.C(C1C=C(C=CC=1F)[C:35]([O:37][CH3:38])=[O:36])#N>O>[C:14]([C:13]1[CH:16]=[C:17]([CH:18]=[CH:19][C:12]=1[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([CH2:2][Br:1])=[N:4]1)[C:35]([O:37][CH3:38])=[O:36])#[N:15]

Participants

5

Reactant 3

HCID 45790123Methyl 3-cyano-4-fluorobenzoateHCID 900376452-(3-Bromomethyl-indazol-1-yl)-benzonitrileHCID 178434273HCID 178434273, compound

Product 1

HCID 90037115Methyl 3-cyano-4-(3-(bromomethyl)-1H-indazol-1-yl)benzoate

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 the product recrystallized from MeOH and in Step 2 1,2-dichoroethane was used in place of CCl4, 3-methyl-1H-indazole (1 g, 7.57 mmol)) and methyl 3-cyano-4-fluorobenzoate (1.36 g, 7.57 mmol) as a white solid.

Workup

  1. customthe product recrystallized from MeOH and in Step 2 1,2-dichoroethane

Sources & evidence

ORD record
ord-9adb3834d4e144f69203b4cdd9d26de0
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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