Benzyl Bromide → 1-Benzyl-2-carboethoxy-4-methoxy-6,7,8,9-tetrahydro-1h-benz[g]indole

HRID 489109Notes

Reaction equation

HRID 489109 reaction equation
[H-].[Na+].[C:3]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[C:14]([O:17][CH3:18])[CH:13]=[C:12]1[CH2:19][CH2:20][CH2:21][CH2:22][C:11]=21)([O:5][CH2:6][CH3:7])=[O:4].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O>[CH2:23]([N:9]1[C:10]2[C:15](=[C:14]([O:17][CH3:18])[CH:13]=[C:12]3[CH2:19][CH2:20][CH2:21][CH2:22][C:11]3=2)[CH:16]=[C:8]1[C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl Bromide2×HCID 24758Sodium hydride2×HCID 111848862-Carboethoxy-4-methoxy-6,7,8,9-tetrahydro-1h-benz[g]indole

Product 1

HCID 112106971-Benzyl-2-carboethoxy-4-methoxy-6,7,8,9-tetrahydro-1h-benz[g]indoleYield 37.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 60% sodium hydride in mineral oil (4.08 g, 0.102 mol) was washed once with hexane and suspended in dry N,N-dimethylformamide (100 mL). 2-Carboethoxy-4-methoxy-6,7,8,9-tetrahydro-1H-benz[g]indole (25.4 g, 92.7 mmol) was added in several portions resulting in gas evolution. Benzyl bromide (12.1 mL, 102 mmol) was added in two portions over 30 min and the resulting mixture stirred for 18 h. Additional portions of 60% sodium hydride suspension (1.30 g) and benzyl bromide (2 mL) were added and the mixture stirred for 27 h. The mixture was poured into water (2 L) and the resulting solution extracted three times with ethyl acetate. The combined extracts were Washed three times with water, dried (sodium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel) provided 12.6 g (37%) of the title compound as a yellow solid: mp 86-88° C. 1H NMR (CDCl3) δ 7.51 (s, 1H), 7.20 (m, 3H), 6.84 (d, J=6.6 Hz, 2H), 6.24 (s, 1H), 6.12 (s, 2H), 4.23 (q, J=7.0 Hz, 2H), 3.93 (s, 3H), 2.96 (m, 2H), 2.85 (m, 2H), 1.71 (m, 4H), 1.30 (t, J=7.0 Hz, 3H); MS ES+ m/e 364 (p+1); IR (CHCl3, cm−1) 2937, 1701, 1502.

Workup

  1. washwas washed once with hexane
  2. customresulting in gas evolution
  3. stirringthe mixture stirred for 27 h
  4. extractionthe resulting solution extracted three times with ethyl acetate
  5. washThe combined extracts were Washed three times with water
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b396431952d4a09b2d491a864f30453
Source dataset
uspto-grants-2005_12
Patent number
US06974831B2

Reaction notes

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