Potassium Carbonate → 3-(pyridin-3-yl)-N-(4-((3-(trifluoromethoxy)phenyl)sulfonyl)phenyl)acrylamide

HRID 1754114노트

반응식

HRID 1754114 반응식
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:5]=[C:6]([S:10]([C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]=[CH:29][C:30](Cl)=[O:31])[CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]=[CH:29][C:30]([NH:17][C:16]2[CH:18]=[CH:19][C:13]([S:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:1])([F:20])[F:21])[CH:5]=3)(=[O:12])=[O:11])=[CH:14][CH:15]=2)=[O:31])[CH:23]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 533991563-Pyridineacrylic acid chlorideHCID 891567704-((3-(Trifluoromethoxy)phenyl)sulfonyl)aniline

생성물 1

HCID 779617403-(pyridin-3-yl)-N-(4-((3-(trifluoromethoxy)phenyl)sulfonyl)phenyl)acrylamide수율 50%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a solution of 4-((3-(trifluoromethoxy)phenyl)sulfonyl)aniline (86, 0.27 mmol) in DMF (3 mL) is added 3-(pyridin-3-yl)acryloyl chloride (58 mg, 0.28 mmol) and K2CO3 (138 mg, 1 mmol). The mixture is heated at 50° C. for 2 h and the solvent is evaporated. The residue is partitioned between EtOAc (15 mL) and brine (10 mL) and the layers are separated. The aqueous layer is extracted with EtOAc (10 mL) and the combined extracts are dried (Na2SO4) and evaporated. Purification of the residue by preparative TLC with 100:5:0.5 CH2Cl2/MeOH/NH4OH gives the titled compounds as a white solid (60 mg, 50%). (LC_MS: M+1 449.14; 1HNMR (400 MHz, DMSO-d6): δ 10.76 (s, 1H), 8.82 (d, 1H), 8.57 (dd, 1H), 7.89-8.06 (m, 7H), 7.76 (t, 1H), 7.74 (m, 1H), 7.66 (d, 1H), 7.46 (dd, 1H), 6.91 (d, 1H).

후처리

  1. customthe solvent is evaporated
  2. customThe residue is partitioned between EtOAc (15 mL) and brine (10 mL)
  3. customthe layers are separated
  4. extractionThe aqueous layer is extracted with EtOAc (10 mL)
  5. dry with materialthe combined extracts are dried (Na2SO4)
  6. customevaporated
  7. customPurification of the residue by preparative TLC with 100:5:0.5 CH2Cl2/MeOH/NH4OH

출처 및 근거

ORD 기록
ord-1ea0799775a1465ab2ed108d61c68888
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169209B2

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