N-bromobutanimide → HCID 22292777、化合物

HRID 84071ノート

反応式

HRID 84071 の反応式
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].[Br:21]N1C(=O)CCC1=O>C(#N)C.CCOC(C)=O>[F:20][C:2]([F:1])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:21])[C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 22292800HCID 22292800、化合物

生成物 1

HCID 22292777HCID 22292777、化合物収率 97.3%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of N-trifluoroacetyl-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (1.25 g, 4.35 mmol) in acetonitrile (40 mL) was treated with N-bromosuccinimide (0.852 g, 4.79 mmol) and stirred overnight at 20 C. The product mixture was diluted with EtOAc (200 mL), washed with saturated aqueous sodium bisulfite (100 mL) and brine (100 mL), dried with Na2SO4 and concentrated. Flash chromatography (15% EtOAc in hexane, silica) resulted in 1.55 g of a clear oil. 1H NMR (400 MHz, CDCl3, mixture of rotamers) d 7.34 (s, 1H), 6.65 (m, 1H), 3.87 (s, 3H), 3.81 (m, 1H), 3.55 (m, 1.3H), 3.37 (m, 0.7H), 3.2-2.9 (bm, 4H), 1.30 (m, 3H). MS calculated for C14H15BrF3NO2+H: 366, observed: 366.

後処理

  1. washwashed with saturated aqueous sodium bisulfite (100 mL) and brine (100 mL)
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-5b3333a4a1834e91a09da185c4d7e0c7
出典データセット
uspto-grants-2014_09
特許番号
US08846906B2

反応ノート

読み込み中…