Cesium carbonate → 2-[(1-Benzyl-2-ethyl-6,7,8,9-tetrahydro-1h-benz[g]indol-4-yl)oxy]acetic acid methyl ester

HRID 489113Notes

Reaction equation

HRID 489113 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([O:21][CH3:22])[CH:13]=[C:14]3[CH2:20][CH2:19][CH2:18][CH2:17][C:15]3=2)[CH:10]=[C:9]1[CH2:23][CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.C(=O)([O-])[O-].[Cs+].[Cs+].BrC[C:37]([O:39][CH3:40])=[O:38]>C(Cl)Cl.O>[CH3:40][O:39][C:37](=[O:38])[CH2:22][O:21][C:12]1[CH:13]=[C:14]2[CH2:20][CH2:19][CH2:18][CH2:17][C:15]2=[C:16]2[C:11]=1[CH:10]=[C:9]([CH2:23][CH3:24])[N:8]2[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 25134Boron tribromideHCID 60984Methyl bromoacetateHCID 113361641-Benzyl-2-ethyl-4-methoxy-6,7,8,9-tetrahydro-1h-benz[g]indole

Product 1

HCID 113149142-[(1-Benzyl-2-ethyl-6,7,8,9-tetrahydro-1h-benz[g]indol-4-yl)oxy]acetic acid methyl esterYield 63.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-benzyl-2-ethyl-4-methoxy-6,7,8,9-tetrahydro-1H-benz[g]indole (660 mg, 2.07 mmol) in methylene chloride (10 mL) was cooled to 0° C. and treated with boron tribromide (0.38 mL, 4.0 mmol). The mixture was stirred for 10 min, poured into ice water, and extracted twice with methylene chloride. The combined methylene chloride layers were washed once with saturated sodium bicarbonate solution, dried (sodium sulfate), filtered, and concentrated in vacuo. The residue was dissolved in N,N-dimethylformamide (10 mL) and treated with cesium carbonate (652 mg, 2.00 mmol) and methyl bromoacetate (0.28 mL, 2.0 mmol) at room temperature for 3 h. The mixture was diluted with water and extracted three times with ether. The combined ether extracts were washed once with water, dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, methylene chloride) provided 479 mg (62%) of the title compound as an off-white solid. 1H NMR (CDCl3) δ 7.25 (m, 3H), 6.85 (d, J=7.6 Hz, 2H), 6.52 (s, 1H), 6.16 (s, 1H), 5.57 (s, 2H), 4.79 (s, 2H), 3.86 (s, 3H), 2.97 (m, 2H), 2.84 (m, 2H), 2.59 (q, J=7.3 Hz, 2H), 1.72 (m, 4H), 1.32 (t, J=7.3 Hz, 3H); MS ES+ m/e 378 (p+1); IR (CHCl3, cm1) 2830, 1756, 1732.

Workup

  1. extractionextracted twice with methylene chloride
  2. washThe combined methylene chloride layers were washed once with saturated sodium bicarbonate solution
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in N,N-dimethylformamide (10 mL)
  7. extractionextracted three times with ether
  8. washThe combined ether extracts were washed once with water
  9. dry with materialdried (magnesium sulfate)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c2fd62053eea44aba55a9cdd87fe4a79
Source dataset
uspto-grants-2005_12
Patent number
US06974831B2

Reaction notes

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