Sodium Carbonate → (R)-(4-(4-(4-(hydroxymethyl)phenyl)phthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone

HRID 1689977노트

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HRID 1689977 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.[OH:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=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]>[OH:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:19])[CH2:14][C@H:13]3[CH3:26])=[N:4][N:3]=2)=[CH:31][CH:30]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 57581487(R)-(4-(4-chlorophthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone

생성물 1

HCID 46891248(R)-(4-(4-(4-(hydroxymethyl)phenyl)phthalazin-1-yl)-3-methylpiperazin-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) (150 mg, 0.409 mmol), 4-(hydroxymethyl)phenylboronic acid (93.2 mg, 0.613 mmol), and tetrakis(triphenylphosphine)palladium (0) (23.6 mg, 0.023 mmol) were dissolved in toluene (4 mL) and aqueous sodium carbonate (2.0 M, 0.400 mL) under an atmosphere of argon. The reaction was heated at 100° C. for 15 hours, then cooled and taken up in ethyl acetate (80 mL). After washing with aqueous K2CO3 (10%), water, and then 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, JK-28. MS (M+H)+=439.2.

후처리

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

출처 및 근거

ORD 기록
ord-59a1d2b6fb274c0f86947e9b9e782a42
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153633B2

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