Cesium carbonate → HCID 67262142、化合物

HRID 410409ノート

反応式

HRID 410409 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([NH:19][C:20]3[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][N:21]=3)[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])O1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:72]1[S:76][CH:75]=[N:74][CH:73]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[S:76]1[C:72]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([NH:19][C:20]3[N:25]=[C:24]([C:26]([F:29])([F:27])[F:28])[CH:23]=[CH:22][N:21]=3)[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:73][N:74]=[CH:75]1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 5460595-BromothiazoleHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67433486Methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}benzoate

生成物 1

HCID 67262142HCID 67262142、化合物収率 72%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

To a flask containing the product of Step 2 (391 mg, 0.92 mmol), dicyclohexyl[2′,4′,6′-tri(propan-2-yl)biphenyl-2-yl]phosphane (44 mg, 0.092 mmol), Pd2(dba)3 (42 mg, 0.046 mmol), cesium carbonate (602 mg, 1.85 mmol) was added a solution of 5-bromothiazole in a degassed mixture of dioxane (8.4 mL) and water (840 μL). The solution was evacuated and then purged with argon 5 times and then heated at 90° C. overnight. The reaction was cooled, diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated. Flash chromatography was used for purification to yield methyl 3-(1,3-thiazol-5-yl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}benzoate (254 mg, 0.67 mmol, 72% yield). MS ESI: [M+H]+ m/z 381.0.

後処理

  1. customThe solution was evacuated
  2. custompurged with argon 5 times
  3. temperatureThe reaction was cooled
  4. additiondiluted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customFlash chromatography was used for purification

出典と根拠

ORDレコード
ord-79ed51a88cc44ae08a6a751b14a0d053
出典データセット
uspto-grants-2014_06
特許番号
US08759366B2

反応ノート

読み込み中…