Cesium carbonate → 3-methyl-N-[3-(pentafluoroethyl)phenyl]-5-(1,3-thiazol-5-yl)aniline

HRID 1039906노트

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HRID 1039906 반응식
Cl[C:2]1N=[C:6]([C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][N:3]=1.[CH3:15][C:16]1[CH:17]=C([CH:20]=[C:21]([C:23]2[S:27][CH:26]=[N:25][CH:24]=2)[CH:22]=1)N.[CH3:28][C:29]1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=C[C:30]1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:15][C:16]1[CH:17]=[C:2]([CH:20]=[C:21]([C:23]2[S:27][CH:26]=[N:25][CH:24]=2)[CH:22]=1)[NH:3][C:4]1[CH:30]=[CH:29][CH:28]=[C:6]([C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])[CH:5]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 584563653-Methyl-5-(1,3-thiazol-5-yl)anilineHCID 866582362-Chloro-4-(pentafluoroethyl)pyrimidine

생성물 1

HCID 866582353-methyl-N-[3-(pentafluoroethyl)phenyl]-5-(1,3-thiazol-5-yl)aniline수율 86.7%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

To a solution of 2-chloro-4-(pentafluoroethyl)pyrimidine (61 mg, 0.26 mmol) and 3-methyl-5-(1,3-thiazol-5-yl)aniline (50 mg, 0.26 mmol) in degassed 1,4-dioxane (1.1 mL) were added Xantphos (23 mg, 0.039 mmol), Pd(OAc)2 (5.9 mg, 0.026 mmol) and Cs2CO3 (172 mg, 0.53 mmol) and the reaction was heated to 100° C. for 30 minutes. After cooling, the reaction was partitioned between EtOAc (10 mL) and saturated aqueous sodium bicarbonate. The layers were separated and the aqueous phase was extracted EtOAc (10 mL). The combined organic phases were washed with saturated aqueous sodium chloride (10 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Purification on silica (20-60% ethyl acetate in hexanes) afforded 3-methyl-N-[3-(pentafluoroethyl)phenyl]-5-(1,3-thiazol-5-yl)aniline (13 mg, 13%) as a colorless foam. MS ESI: [M+H]+ m/z 387.0.

후처리

  1. temperatureAfter cooling
  2. customthe reaction was partitioned between EtOAc (10 mL) and saturated aqueous sodium bicarbonate
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted EtOAc (10 mL)
  5. washThe combined organic phases were washed with saturated aqueous sodium chloride (10 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification on silica (20-60% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-dcad3f042072443ca4bed0e8137b1bb5
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551984B2

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