Hydroxylamine → Furo[3,2-c]pyridin-4-amine

HRID 250026

反応式

HRID 250026 の反応式
Cl[C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][N:3]=1.CC(C)([O-])C.[Na+].C(=[NH:30])(C1C=CC=CC=1)C1C=CC=CC=1.NO>C1(C)C=CC=CC=1.CCOCC.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].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>[O:10]1[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:30])[C:7]=2[CH:8]=[CH:9]1

参加物

9

反応物 4

HCID 787HydroxylamineHCID 136809Benzophenone imineHCID 27797464-Chlorofuro[3,2-c]pyridineHCID 23676156Sodium t-butoxide

生成物 1

HCID 22665882Furo[3,2-c]pyridin-4-amine収率 89.1%

試薬・触媒・溶媒 4

HCID 634876Binap, (A+-)-触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
80 °C

実験手順

To 4-chlorofuro[3,2-c]pyridine (1 g, 6.5 mmol) in toluene under nitrogen was added racemic BINAP (0.243 g, 0.4 mmol), Pd2(dba)3 (0.12 g, 0.13 mmol) and sodium tert-butoxide (0.88 g, 9.1 mmol). Benzophenoneimine (1.3 mL, 7.81 mmol) was added and the mixture was heated to 80° C. for 3 h and cooled to room temperature. The reaction mixture was diluted with ether, filtered through Celite, and washed with ether. The filtrate was concentrated and the deep orange residue was taken up in methanol (90 ml) and treated with hydroxylamine (1.2 mL, 19.5 mmol). The mixture was stirred at ambient temperature for 18 h and concentrated. The residue was purified by column chromatography (95-100% ethyl acetate/hexanes) to afford furo[3,2-c]pyridin-4-amine (776 mg, 5.79 mmol, 89% yield) as a deep orange solid. MS (LC/MS) R.T.=0.51; [M+H]+=135.02.

後処理

  1. temperaturecooled to room temperature
  2. filtrationfiltered through Celite
  3. washwashed with ether
  4. concentrationThe filtrate was concentrated
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (95-100% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-5e649b185f8848978c1c3769bdf69041
出典データセット
uspto-grants-2011_01
特許番号
US07863291B2

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