Cesium carbonate → 6-(5-isopropyl-2-methylphenyl)-4-methoxy-2-(5-methyl-1-tosyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 80797

反応式

HRID 80797 の反応式
[CH3:1][O:2][C:3]1[C:4]2[CH2:32][NH:31][CH2:30][CH2:29][C:5]=2[N:6]=[C:7]([C:9]2[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[N:12][N:13]3[S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[N:8]=1.FC(F)(F)S(O[C:39]1[CH:44]=[C:43]([CH:45]([CH3:47])[CH3:46])[CH:42]=[CH:41][C:40]=1[CH3:48])(=O)=O.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.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]>[CH:45]([C:43]1[CH:42]=[CH:41][C:40]([CH3:48])=[C:39]([N:31]2[CH2:30][CH2:29][C:5]3[N:6]=[C:7]([C:9]4[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]5[C:10]=4[CH:11]=[N:12][N:13]5[S:19]([C:22]4[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[N:8]=[C:3]([O:2][CH3:1])[C:4]=3[CH2:32]2)[CH:44]=1)([CH3:47])[CH3:46]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 130964092-Methyl-5-(propan-2-yl)phenyl trifluoromethanesulfonateHCID 712406574-methoxy-2-(5-methyl-1-tosyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

生成物 1

HCID 712404896-(5-isopropyl-2-methylphenyl)-4-methoxy-2-(5-methyl-1-tosyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
140 °C

実験手順

A mixture of 4-methoxy-2-(5-methyl-1-tosyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (250 mg, 0.556 mmol), 5-isopropyl-2-methylphenyl trifluoromethanesulfonate (235 mg, 0.834 mmol), X-Phos (53.0 mg, 0.111 mmol), Pd2(dba)3 (50.9 mg, 0.056 mmol), and Cs2CO3 (362 mg, 1.11 mmol) in THF (3 mL) was heated in a microwave reactor at 140° C. for 60 min. The reaction mixture was partitioned between EtOAc and water. The organic layer was washed with brine, dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (0-50% EtOAc/heptane) to provide 6-(5-isopropyl-2-methylphenyl)-4-methoxy-2-(5-methyl-1-tosyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. MS (ESI+) m/z 582.1 (M+H)+.

後処理

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (0-50% EtOAc/heptane)

出典と根拠

ORDレコード
ord-454013d396d340aa937bb3762e16e56d
出典データセット
uspto-grants-2014_09
特許番号
US08846656B2

関連ノート

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