Cesium carbonate → [2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-4-yl]-(2,6-dimethylpyrimidin-4-yl)amine

HRID 626660

反応式

HRID 626660 の反応式
Cl[C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=[C:6]2[CH:5]=[CH:4][N:3]=1.[NH2:19][C:20]1[CH:25]=[C:24]([CH3:26])[N:23]=[C:22]([CH3:27])[N:21]=1.CC1(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=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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]>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[N:9]1[CH:8]=[C:7]2[C:2]([NH:19][C:20]3[CH:25]=[C:24]([CH3:26])[N:23]=[C:22]([CH3:27])[N:21]=3)=[N:3][CH:4]=[CH:5][C:6]2=[N:10]1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 680392,6-Dimethyl-4-aminopyrimidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866970364-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

生成物 1

HCID 69671258[2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine-4-yl]-(2,6-dimethylpyrimidin-4-yl)amine収率 86.1%

試薬・触媒・溶媒 2

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

実験手順

A suspension of 4-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (200 mg, 0.57 mmol), 4-amino-2,6-dimethylpyrimidine (95 mg, 0.77 mmol), Pd2(dba)3 (16 mg, 0.018 mmol), Xantphos (39 mg, 0.067 mmol) and cesium carbonate (437 mg, 1.34 mmol) in dioxane (5 mL) was sealed in a microwave vial, purged with nitrogen and irradiated at 150° C. for 25 minutes in the microwave. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (60-80% ethyl acetate in cyclohexane) to afford the title compound as a yellow solid (189 mg, 73% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.52 (br s, 1H), 9.16 (s, 1H), 8.34 (s, 1H), 7.99 (d, J=6.4 Hz, 1H), 7.83 (d, J=1.0 Hz, 1H), 7.81 (s, 1H), 7.71 (dd, J=9.0, 7.3 Hz, 1H), 7.21 (d, J=6.4 Hz, 1H), 3.32 (s, 3H), 2.41 (s, 3H). LCMS (Method B): RT=2.93 min, m/z: 385 [M+H+].

後処理

  1. customwas sealed in a microwave vial
  2. custompurged with nitrogen
  3. customirradiated at 150° C. for 25 minutes in the microwave
  4. temperatureThe reaction mixture was cooled
  5. custompartitioned between ethyl acetate and water
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel flash chromatography (60-80% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-d5679c8a3f054827b0927fe2043be0bd
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

関連ノート

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