Dichloromethane → HCID 178487940、化合物

HRID 245745

反応式

HRID 245745 の反応式
Br[C:2]1[N:3]=[C:4]([C@H:12]2[CH2:17][CH2:16][C@H:15]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=12.[CH3:25][O:26][C:27]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[CH:30][C:28]=1[NH2:29].C(=O)([O-])[O-].[K+].[K+].ClCCl>O1CCOCC1.C(#N)C>[CH3:25][O:26][C:27]1[CH:33]=[C:32]([C:2]2[N:3]=[C:4]([C@H:12]3[CH2:17][CH2:16][C@H:15]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)[CH2:14][CH2:13]3)[N:5]3[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=23)[CH:31]=[CH:30][C:28]=1[NH2:29]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 177502072-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 178432912HCID 178432912、化合物

生成物 1

HCID 178487940HCID 178487940、化合物収率 37.1%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
89 °C

実験手順

To a suspension of 1-bromo-8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazine (0.714 mmol, 280 mg) and 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.714 mmol, 178 mg) in dioxane (5 mL) was added aqueous 2M potassium carbonate (3.57 mmol, 1.78 mL). The mixture was degassed and put under a nitrogen atmosphere. Then 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride complex with dichloromethane (0.050 mmol, 40.4 mg) was added and the reaction mixture was heated to 89° C. After three hours the reaction mixture was diluted with acetonitrile (9 ml) and filtered over decalite. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (silica gel; gradient of dichloromethane to dichloromethane/methanol 5/1) to give 2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)aniline (115 mg).

後処理

  1. customThe mixture was degassed
  2. filtrationfiltered over decalite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by column chromatography (silica gel; gradient of dichloromethane to dichloromethane/methanol 5/1)

出典と根拠

ORDレコード
ord-13660ae0602c4d3fa3e8d6f6075710bc
出典データセット
uspto-grants-2014_02
特許番号
US08658794B2

関連ノート

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