Sodium Carbonate → ((R)-3-methyl-4-(4-(4-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)phenyl)phthalazin-1-yl)piperazin-1-yl)(phenyl)methanone

HRID 1689980노트

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HRID 1689980 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:19])[CH2:14][C@H:13]2[CH3:26])=[N:4][N:3]=1.[O:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]1[O:33][CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.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]>[CH3:26][C@H:13]1[N:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([C:39]3[CH:40]=[CH:41][C:36]([CH2:35][CH2:34][O:33][CH:28]4[CH2:29][CH2:30][CH2:31][CH2:32][O:27]4)=[CH:37][CH:38]=3)=[N:3][N:4]=2)[CH2:17][CH2:16][N:15]([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])[CH2:14]1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 44890903(4-(2-((Tetrahydro-2H-pyran-2-yl)oxy)ethyl)phenyl)boronic acidHCID 57581487(R)-(4-(4-chlorophthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone

생성물 1

HCID 57581517((R)-3-methyl-4-(4-(4-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)phenyl)phthalazin-1-yl)piperazin-1-yl)(phenyl)methanone

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

(R)-(4-(4-chlorophthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone (JK-5) (200 mg, 0.545 mmol), 4-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)phenylboronic acid (136 mg, 0.545 mmol) and tetrakis(triphenylphosphine)palladium (0) (31.5 mg, 0.0273 mmol) were dissolved in toluene (4 mL) and aqueous sodium carbonate (2.0M, 0.400 mL) under an atmosphere of argon. The reaction was heated at 100° C. for 15 hours, cooled to rt, and taken up in ethyl acetate (80 mL). After washing with aqueous K2CO3 (10%), water, and saturated sodium chloride, the organics were dried (MgSO4) and evaporated to give a yellow oil. Chromatography over silica gel with a gradient of hexanes/0-100% ethyl acetate gave a pale yellow solid, compound 83. MS (M+H)+=537.4.

후처리

  1. temperaturecooled to rt
  2. washAfter washing with aqueous K2CO3 (10%), water, and saturated sodium chloride
  3. dry with materialthe organics were dried (MgSO4)
  4. customevaporated
  5. customto give a yellow oil

출처 및 근거

ORD 기록
ord-3c1c5f9389d44beb9673948826da1446
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153633B2

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