Binap, (A+-)- → 4-chloro-6-(2-pyrrol-1-yl-benzylamino)-2H-phthalazin-1-one

HRID 1667479ノート

反応式

HRID 1667479 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][N:6]=[C:5]2[Cl:13].[N:14]1([C:19]2[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=2[CH2:21][NH2:22])[CH:18]=[CH:17][CH:16]=[CH:15]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>CC(N(C)C)=O.CCOC(C)=O.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]>[Cl:13][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:22][CH2:21][C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[N:14]3[CH:18]=[CH:17][CH:16]=[CH:15]3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

参加物

8

反応物 4

HCID 634876Binap, (A+-)-HCID 7073272-(1-Pyrrolyl)benzylamineHCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

生成物 1

HCID 249483444-chloro-6-(2-pyrrol-1-yl-benzylamino)-2H-phthalazin-1-one収率 16.3%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

実験手順

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.578 mmol), 2-(1-pyrrolyl)benzylamine (122 mg, 0.708 mmol), Pd2(dba)3 (56 mg, 0.061 mmol), rac-BINAP (108 mg, 0.173 mmol) and NaOtBu (139 mg, 1.445 mmol) in DMA (5 mL) was heated at 85° C. for 1.5 h. The mixture was allowed to cool, diluted with EtOAc and washed with water. The organic layer was washed with sat.aq. NaHCO3, brine and dried (Na2SO4). Chromatography on silica (EtOAc/hexanes) afforded 4-chloro-6-(2-pyrrol-1-yl-benzylamino)-2H-phthalazin-1-one (33 mg) as an off white solid, 1H (400 MHz, d6-DMSO) δ: 4.22 (d, 2H), 6.26 (t, 2H), 6.60 (bs, 1H), 7.04 (t, 2H), 7.08 (d, 1H), 7.35 (m, 1H), 7.40 (m, 2H), 7.49 (m, 1H), 7.62 (t, 1H), 7.91 (d, 1H) ppm; m/z (M+1) 350.97.

後処理

  1. temperatureto cool
  2. washwashed with water
  3. washThe organic layer was washed with sat.aq
  4. dry with materialNaHCO3, brine and dried (Na2SO4)

出典と根拠

ORDレコード
ord-a4fddd81b3be42d984461d13a927debb
出典データセット
uspto-grants-2011_10
特許番号
US08044041B2

反応ノート

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