Methyl iodide → tert-Butyl 7-bromo-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

HRID 930608

반응식

HRID 930608 반응식
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13][C:9]=3[NH:10][C:11]=2[CH:12]=1.[CH3:24]I>CN(C=O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13][C:9]=3[N:10]([CH3:24])[C:11]=2[CH:12]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57950374tert-butyl 7-bromo-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

생성물 1

HCID 57950375tert-Butyl 7-bromo-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate수율 91%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium hydride (60% weight dispersion in mineral oil, 4.19 g, 0.105 mol) was added portionwise to a solution of tert-butyl 7-bromo-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (23.6 g, 0.07 mol) in DMF (300 mL) at room temperature under N2. After 1 h, methyl iodide (14.8 g, 6.47 mL, 0.105 mol) was added, and the reaction was allowed to proceed for an additional 2 h. The mixture was quenched with H2O, upon which a solid precipitated out of solution. The suspension was therefore diluted to 2 L with H2O and filtered. The solids were washed thoroughly with water, then dissolved in CH2Cl2, dried over Na2SO4, filtered and concentrated to dryness. This provided the title compound (22.4 g, 91%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 7.41 (s, 1H), 7.30 (d, J=8.3 Hz, 1H), 7.17 (d, J=8.4 Hz, 1H), 4.60 (s, 2H), 3.81 (br t, 2H), 3.58 (s, 3H), 2.77 (t, J=5.4 Hz, 2H), 1.50 (s, 9H).

후처리

  1. waitto proceed for an additional 2 h
  2. customThe mixture was quenched with H2O, upon which a solid
  3. customprecipitated out of solution
  4. additionThe suspension was therefore diluted to 2 L with H2O
  5. filtrationfiltered
  6. washThe solids were washed thoroughly with water
  7. dissolutiondissolved in CH2Cl2
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-c6126ea26f40492283dfcc0fe546779e
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296743B2

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