2-Bromobenzaldehyde → (E)-3-[2-(2-bromophenyl)vinyl]-1H-indazole

HRID 1821339Notes

Reaction equation

HRID 1821339 reaction equation
[Br-].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:3]1.C1CCN2C(=NCCC2)CC1.[Br:42][C:43]1[CH:50]=[CH:49][CH:48]=[CH:47][C:44]=1[CH:45]=O>CO>[Br:42][C:43]1[CH:50]=[CH:49][CH:48]=[CH:47][C:44]=1/[CH:45]=[CH:11]/[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:2][N:3]=1

Participants

5

Reactant 3

HCID 811292-BromobenzaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178419401HCID 178419401, compound

Product 1

HCID 69000164(E)-3-[2-(2-bromophenyl)vinyl]-1H-indazoleYield 12%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1H-indazol-3-ylmethyl)triphenylphosphonium bromide (3.0 g, 6.3 mmol) in methanol (18 mL), DBU (1.4 mL, 9.5 mmol) was added dropwise and 2-bromobenzaldehyde (0.81 mL, 7.0 mmol) was further added, followed by stirring at room temperature for 1.5 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 95/5). The obtained compound was washed with methanol (15 mL) and dried under reduced pressure to obtain (E)-3-[2-(2-bromophenyl)vinyl]-1H-indazole (0.22 g, 12%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 95/5)
  3. washThe obtained compound was washed with methanol (15 mL)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-714b57f19eff42c1972741f309613f1a
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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