Dimethylformamide → (5-fluoro-3-methylbenzo[b]thiophen-2-yl)-N-methylmethanamine

HRID 1711820ノート

反応式

HRID 1711820 の反応式
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[S:6][CH:7]=[C:8]([CH3:9])[C:4]=2[CH:3]=1.C([Li])CCC.[CH3:17][N:18](C=O)[CH3:19].[NH4+].[Cl-]>C1COCC1>[F:1][C:2]1[CH:11]=[CH:10][C:5]2[S:6][C:7]([CH2:17][NH:18][CH3:19])=[C:8]([CH3:9])[C:4]=2[CH:3]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 5968285-Fluoro-3-methyl-benzo[b]thiopheneHCID 178418339Butyllithium

生成物 1

HCID 59456918(5-fluoro-3-methylbenzo[b]thiophen-2-yl)-N-methylmethanamine収率 97%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-fluoro-3-methyl-benzo[b]thiophene (4.83 g, 29.1 mmol) in THF (50 mL) at −30° C. under N2 was added n-butyllithium (20.0 mL of a 1.6 M solution in hexanes, 32.0 mmol) dropwise. The resulting orange solution was stirred for 1 h and then DMF (3.4 mL, 43.7 mmol) was added in one portion. The solution was warmed slowly to room temperature and stirred overnight. Saturated aqueous NH4Cl was added and the mixture was extracted with ethyl acetate (3×200 mL). The combined organics were washed with water (100 mL) and brine (100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound (5.55 g, 97%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 10.32 (s, 1H), 7.80 (dd, J=9.0, 4.8 Hz, 1H), 7.53 (d J=9.3, 2.6 Hz, 1H), 7.31-7.24 (m, 1H), 2.76 (s, 3H).

後処理

  1. stirringstirred overnight
  2. extractionthe mixture was extracted with ethyl acetate (3×200 mL)
  3. washThe combined organics were washed with water (100 mL) and brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-09c940a8b812404abb136852aeba5f0c
出典データセット
uspto-grants-2010_09
特許番号
US07790709B2

反応ノート

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