Bromine → HCID 178519632, compound

HRID 913820Notes

Reaction equation

HRID 913820 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH:12]=[O:13])[CH:11]=1)[NH:8][N:7]=[CH:6]2.[Br:16]Br>C(O)(=O)C.C(Cl)Cl>[Br:16][C:6]1[C:5]2[C:9](=[C:10]([CH:12]=[O:13])[CH:11]=[C:3]([C:2]([F:1])([F:14])[F:15])[CH:4]=2)[NH:8][N:7]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 575462105-(trifluoromethyl)-1H-indazole-7-carbaldehyde

Product 1

HCID 178519632HCID 178519632, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-(trifluoromethyl)-1H-indazole-7-carbaldehyde (270 mg, 1.26 mmol) in acetic acid (5 mL) was added bromine (97 μL, 1.89 mmol) slowly over 5 min. After 1 h, the reaction mixture was diluted with methylene chloride, washed with water (2×), saturated sodium thiosulfate (2×), saturated sodium bicarbonate (2×), brine (2×), dried over sodium sulfate, and concentrated to afford 340 mg (92%) as a yellow powder. 1H-NMR (CDCl3, 300 MHz) δ 10.18 (s, 1H), 8.22 (s, 1H), 8.15 (s, 1H). Mass spec.: 294.81 (MH)+.

Workup

  1. washwashed with water (2×), saturated sodium thiosulfate (2×), saturated sodium bicarbonate (2×), brine (2×)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customto afford 340 mg (92%) as a yellow powder

Sources & evidence

ORD record
ord-8903e6478d4843a4aa5885914fe41c70
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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