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

HRID 1404140노트

반응식

HRID 1404140 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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].

후처리

  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)

출처 및 근거

ORD 기록
ord-acc38da7f7b04094bdc1b47b3c43c1d0
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912220B2

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