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 1689980ノート

反応式

HRID 1689980 の反応式
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

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-3c1c5f9389d44beb9673948826da1446
出典データセット
uspto-grants-2012_04
特許番号
US08153633B2

反応ノート

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