Dimethylformamide → HCID 10223886, compound

HRID 489102Notes

Reaction equation

HRID 489102 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([O:20][CH3:21])[CH:13]=[C:14]3[CH2:19][CH2:18][CH2:17][C:15]3=2)[CH:10]=[C:9]1[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.[C:27](=[O:30])([O-])[O-].[Cs+].[Cs+].BrC[C:35]([O:37][CH3:38])=[O:36].C[N:40](C)[CH:41]=[O:42]>C(Cl)(Cl)Cl.O>[CH3:38][O:37][C:35](=[O:36])[CH2:21][O:20][C:12]1[CH:13]=[C:14]2[CH2:19][CH2:18][CH2:17][C:15]2=[C:16]2[C:11]=1[C:10]([C:27](=[O:30])[C:41]([NH2:40])=[O:42])=[C:9]([CH3:22])[N:8]2[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 25134Boron tribromideHCID 60984Methyl bromoacetateHCID 11312366HCID 11312366, compound

Product 1

HCID 10223886HCID 10223886, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

A solution of 1-benzyl-2-methyl-4-methoxy-1,6,7,8-tetrahydrocyclopent[g]indole (2.2 g, 7.6 mmol) in chloroform (40 mL) was treated with boron tribromide (2.8 mL, 30 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 2.5 h. The mixture was poured into water and extracted with chloroform. The organic layer was washed once with water, once with saturated sodium chloride solution, dried (sodium sulfate), filtered, and concentrated in vacuo to provide an oil. A solution of this material (oil) in N,N-dimethylformamide (35 mL) was treated with cesium carbonate (3.21 g, 9.10 mmol) and methyl bromoacetate (0.86 mL, 9.1 mmol) at room temperature. After stirring for 18 h, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed once with water, once with saturated sodium chloride solution, dried (sodium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 10% ethyl acetate/90% hexanes) provided 0.43 g (16%) of the title product as a white solid: mp 135-138° C. 1H NMR (CDCl3) δ 7.22 (m, 3H), 6.88 (d, J=7.0 Hz, 2H), 6.47 (s, 1H), 6.36 (s, 1H), 5.42 (s, 2H), 4.76 (s, 2H), 3.82 (s, 3H), 3.00 (t, J=7.3 Hz, 2H), 2.90 (t, J=7.3 Hz, 2H), 2.29 (s, 3H), 2.04 (quintet, J=7.0 Hz, 2H); MS ES+ m/e 350 (p+1); IR (CHCl3, cm−1) 2955, 1760, 1737, 1496.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed once with water, once with saturated sodium chloride solution
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide an oil
  7. stirringAfter stirring for 18 h
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed once with water, once with saturated sodium chloride solution
  10. dry with materialdried (sodium sulfate)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-838cf3f68a1d424fa0e163616081d391
Source dataset
uspto-grants-2005_12
Patent number
US06974831B2

Reaction notes

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