Dichloromethane → HCID 178487940, 화합물

HRID 245745

반응식

HRID 245745 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 178487940HCID 178487940, 화합물수율 37.1%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 312751,4-Dioxane용매

반응 조건

온도
89 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-13660ae0602c4d3fa3e8d6f6075710bc
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658794B2

연결된 노트

불러오는 중…