Water → 1-[1-(3,5-Bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1h-[1,2,3]triazol-4-yl]-2-bromo-3-(2-chloro-phenyl)-propane-1,3-dione

HRID 2251987

Reaction equation

HRID 2251987 reaction equation
[Br:1]Br.[F:3][C:4]([F:40])([F:39])[C:5]1[CH:6]=[C:7]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[CH2:8][N:9]1[C:13]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[C:12]([C:20](=[O:31])[CH2:21][C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])=[O:23])[N:11]=[N:10]1.O>C(Cl)Cl>[F:40][C:4]([F:3])([F:39])[C:5]1[CH:6]=[C:7]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[CH2:8][N:9]1[C:13]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[C:12]([C:20](=[O:31])[CH:21]([Br:1])[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])=[O:23])[N:11]=[N:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 866012491-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1H-[1,2,3]triazol-4-yl]-3-(2-chloro-phenyl)-propane-1,3-dione

Product 1

HCID 877163621-[1-(3,5-Bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1h-[1,2,3]triazol-4-yl]-2-bromo-3-(2-chloro-phenyl)-propane-1,3-dioneYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add bromine (28 μL, 0.54 mmol) to a mixture of 1-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1H-[1,2,3]triazol-4-yl]-3-(2-chloro-phenyl)-propane-1,3-dione (256 mg, 0.463 mmol) in 1:1 CH2Cl2:H2O (4 mL). Stir mixture at RT for 30 min, then dilute with additional CH2Cl2 (20 mL) and wash with NaHCO3 (20 mL). Dry, filter, and concentrate the organic layer to give the title compound (287 mg, 98%). MS (IS) 553.2 (M+1), MS (ES−) 551.2 (M−1). 1HNMR (400 MHz, CDCl3): δ 7.80 (m, 1H), 8.53 (m, 1H), 7.85 (m, 2H), 7.63 (m, 1H), 7.46 (m, 7H), 7.04 (s, 1H), 5.60 (m, 2H).

Workup

  1. washwash with NaHCO3 (20 mL)
  2. customDry
  3. filtrationfilter
  4. concentrationconcentrate the organic layer

Sources & evidence

ORD record
ord-2073e7fae4364e49bb53ea490c36dc36
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Linked notes

Loading…