Sodium Carbonate → 7-[3-(2-Methyl-2H-[1,2,3]triazol-4-yl)phenyl]-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine

HRID 586312노트

반응식

HRID 586312 반응식
CC1(C)COB([C:8]2[CH:9]=[C:10]([C:14]3[CH:18]=[N:17][N:16]([CH3:19])[N:15]=3)[CH:11]=[CH:12][CH:13]=2)OC1.Br[C:22]1[N:26]2[N:27]=[CH:28][C:29]([C:31]([F:34])([F:33])[F:32])=[N:30][C:25]2=[N:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:19][N:16]1[N:15]=[C:14]([C:10]2[CH:9]=[C:8]([C:22]3[N:26]4[N:27]=[CH:28][C:29]([C:31]([F:32])([F:33])[F:34])=[N:30][C:25]4=[N:24][CH:23]=3)[CH:13]=[CH:12][CH:11]=2)[CH:18]=[N:17]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazineHCID 22329492HCID 22329492, 화합물

생성물 1

HCID 101545907-[3-(2-Methyl-2H-[1,2,3]triazol-4-yl)phenyl]-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine수율 34%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

This reaction was carried out as described in Example 37, step e, using 4-[3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)phenyl]-2-methyl-2H-[1,2,3]triazole (190 mg, 0.7 mmol), 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.156 g, 0.585 mmol), 2 M Na2CO3 (0.70 ml) and tetrakis(triphenylphosphine)palladium(0) (0.034 g) in 1,2-dimethoxyethane (2 ml). The crude residue was purified by flash chromatography (silica gel, 50% Et2O/toluene) and crystallized from toluene to yield the title compound (68 mg, 34%): 1H NMR (400 MHz, CDCl3) δ 4.28 (3H, s), 7.63 (1H, t, J 7.8 Hz), 7.87 (1H, dt, J 7.8, 1.4 Hz), 7.91 (1H, s), 8.05-8.09 (1H, m), 8.52 (1H, t, J 1.4 Hz), 8.68 (1H, s), 8.85 (1H, s); MS (ES+) m/z 346 [M+H]+.

후처리

  1. customThe crude residue was purified by flash chromatography (silica gel, 50% Et2O/toluene)
  2. customcrystallized from toluene

출처 및 근거

ORD 기록
ord-c3f4d7c0b39c4c82b5a97ff5cfa42e8a
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936608B2

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