Potassium Carbonate → 2-{3-[2-Chloro-4-(4-chloro-2-methyl-phenylamino)-benzoyl]-4-fluoro-phenoxy}-N-methyl-acetamide

HRID 1012660

반응식

HRID 1012660 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[CH3:16])[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:20]=1[F:26])=[O:18].Cl[CH2:28][C:29]([NH:31][CH3:32])=[O:30].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[CH3:16])[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([CH:22]=[CH:21][C:20]=1[F:26])[O:25][CH2:28][C:29]([NH:31][CH3:32])=[O:30])=[O:18]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 667732-chloro-N-methylacetamideHCID 67313338[2-Chloro-4-(4-chloro-2-methyl-phenylamino)-phenyl]-(2-fluoro-5-hydroxy-phenyl)-methanone

생성물 1

HCID 586775312-{3-[2-Chloro-4-(4-chloro-2-methyl-phenylamino)-benzoyl]-4-fluoro-phenoxy}-N-methyl-acetamide

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
130 °C

실험 절차

Compound 513 (36 mg, 0.09 mmol) was dissolved in acetonitrile (2 mL) in a reaction vial. 2-Chloro-N-methyl-acetamide (30 mg, 0.28 mmol), K2CO3 (38 mg, 0.28 mmol) were added. The reaction vial was flushed with argon, closed and then stirred at 130° C. for 45 min. in a microwave oven. The reaction mixture was poured into a mixture of EtOAc:H2O (1:1, 10 mL). The layers were separated and the aqueous phase was extracted with EtOAc (3×5 mL). The combined organic layers were dried (MgSO4), filtered, concentrated in vacuo and purified by continuously gradient flash chromatography using EtOAc/petroleum ether (40-60)(v:v=1:3 to 100:0) as the eluent, affording the title compound as a yellow oil. 13C NMR (CDCl3) δ 190.1, 168.2, 155.7 (d), 153.2 (d), 149.2, 136.6, 135.0, 134.5, 133.4, 131.2, 130.5, 128.7 (d), 128.1, 127.1, 125.3, 119.6 (d), 117.4 (d), 116.1 (d), 115.6, 112.4, 68.0, 25.8, 17.9

후처리

  1. customThe reaction
  2. customvial was flushed with argon
  3. customclosed
  4. additionThe reaction mixture was poured into a mixture of EtOAc:H2O (1:1, 10 mL)
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with EtOAc (3×5 mL)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. custompurified by continuously gradient flash chromatography

출처 및 근거

ORD 기록
ord-394ec7c6d0e64cae974394d43fad958c
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977387B2

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