Sodium Sulfate → 2-(4-(3-chlorobenzyloxy)-5-fluoro-1-methyl-1H-indol-3-yl)-N-methyl ethanamine

HRID 1404140ノート

反応式

HRID 1404140 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[C:15]([F:16])=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9]([CH2:18][C:19]([NH:21][CH3:22])=O)=[CH:10][N:11]2[CH3:17].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Al+3].[Cl-].[Cl-].[Cl-].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[C:15]([F:16])=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9]([CH2:18][CH2:19][NH:21][CH3:22])=[CH:10][N:11]2[CH3:17]

参加物

7

反応物 4

HCID 24436Sodium SulfateHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 583039872-(4-(3-chlorobenzyloxy)-5-fluoro-1-methyl-1H-indol-3-yl)-N-methyl acetamide

生成物 1

HCID 509973972-(4-(3-chlorobenzyloxy)-5-fluoro-1-methyl-1H-indol-3-yl)-N-methyl ethanamine収率 23%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 33-7 (50 mg, 0.139 mmol) in THF (10 mL) was added dropwise into the solution of lithium aluminum hydride (19 mg, 0.417 mmol) and AlCl3 (41 mg, 0.381 mmol) in THF (10 mL). The mixture was stirred at room temperature for 1 h. Na2SO4.10 H2O was added to quench the reaction. The solid was filtered off and washed with ethyl acetate (20 mL). The organic solvent was washed with brine (3×30 mL), dried over MgSO4, filtered and evaporated. The resulting residue was purified by preparative HPLC (acid condition, water/CH3CN, 30-35% CH3CN in 7.5 min, RT=6.5 min) to give 33-8 (11 mg, 23%) as a yellow solid. 1H-NMR (400 MHz, CDCl3): δ (ppm) 8.80-8.60 (brs, 1H), 7.47 (s, 1H), 7.34 (s, 2H), 7.28 (s, 1H), 7.02-6.99 (m, 1H), 6.92-6.89 (m, 2H), 5.25 (s, 2H), 3.66 (s, 3H), 3.13-3.05 (m, 4H), 2.45 (s, 3H). LRMS: calc and found: 347.1 [M+1].

後処理

  1. customto quench
  2. customthe reaction
  3. filtrationThe solid was filtered off
  4. washwashed with ethyl acetate (20 mL)
  5. washThe organic solvent was washed with brine (3×30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe resulting residue was purified by preparative HPLC (acid condition, water/CH3CN, 30-35% CH3CN in 7.5 min, RT=6.5 min)

出典と根拠

ORDレコード
ord-acc38da7f7b04094bdc1b47b3c43c1d0
出典データセット
uspto-grants-2014_12
特許番号
US08912220B2

反応ノート

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