Sodium Carbonate → 1-{3-[7-(4-Fluoro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-phenyl}-3-(2,2,2-trifluoro-ethyl)-urea

HRID 341231

반응식

HRID 341231 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14](I)=[CH:15][N:16]=[C:10]3[CH:9]=2)=[CH:4][CH:3]=1.Br[C:19]1[CH:20]=[C:21]([NH:25][C:26]([NH:28][CH2:29][C:30]([F:33])([F:32])[F:31])=[O:27])[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.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>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14]([C:23]4[CH:22]=[C:21]([NH:25][C:26]([NH:28][CH2:29][C:30]([F:31])([F:32])[F:33])=[O:27])[CH:20]=[CH:19][CH:24]=4)=[CH:15][N:16]=[C:10]3[CH:9]=2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 472525331-(3-Bromophenyl)-3-(2,2,2-trifluoroethyl)ureaHCID 593207767-(4-Fluoro-phenyl)-3-iodo-imidazo[1,2-a]pyridine

생성물 1

HCID 565896261-{3-[7-(4-Fluoro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-phenyl}-3-(2,2,2-trifluoro-ethyl)-urea수율 76.8%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

A mixture of 7-(4-fluoro-phenyl)-3-iodo-imidazo[1,2-a]pyridine (10.1 g, 29.8 mmol), 1-(3-bromo-phenyl)-3-(2,2,2-trifluoro-ethyl)-urea (12.3 g, 35.8 mmol) and 2M sodium carbonate (120 mL) in dimethoxyethane (595 mL) was deoxygenated by evacuation/refill with N2 (×3). Tetrakis(triphenylphosphine)palladium (1.72 g, 1.49 mmol) was added, the resulting mixture was deoxygenated again (×3) and then heated at 80° C. under N2 overnight. The reaction was allowed to cool to RT, and solvents were removed under reduced pressure. The crude mixture was diluted with water (100 mL), EtOAc (100 mL) and DCM (100 mL) with stirring. The resulting slurry was filtered, the solid was washed with EtOAc and dried under vacuum to give the title compound (9.8 g). 1H NMR (400 MHz, DMSO-d6) δ 8.98 (1H, s), 8.61 (1H, d), 7.99 (1H, s), 7.96-7.87 (2H, m), 7.79 (2H, s), 7.45 (2H, d), 7.41-7.30 (3H, m), 7.30-7.23 (1H, m), 6.87 (1H, bt), 4.00-3.89 (2H, m). MS: [M+H]+ 429

후처리

  1. customwas deoxygenated by evacuation/refill with N2 (×3)
  2. customthe resulting mixture was deoxygenated again (×3)
  3. temperatureto cool to RT
  4. customsolvents were removed under reduced pressure
  5. additionThe crude mixture was diluted with water (100 mL), EtOAc (100 mL) and DCM (100 mL)
  6. filtrationThe resulting slurry was filtered
  7. washthe solid was washed with EtOAc
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-6ca39044fa4d4fa8b185b2d127ad17e2
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895745B2

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