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

HRID 1039906ノート

反応式

HRID 1039906 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-dcad3f042072443ca4bed0e8137b1bb5
出典データセット
uspto-grants-2013_10
特許番号
US08551984B2

反応ノート

読み込み中…