Cesium carbonate → HCID 10274713, compound

HRID 895937Notes

Reaction equation

HRID 895937 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:14]=[C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]2=[C:11]2[C:7]=1[CH:8]=[C:9]([CH3:26])[N:10]2[CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C1(C[N:35]2C3C(=C(OC)C=C4C=CC=CC4=3)C=C2C)CCCCC1.B(Br)(Br)Br.BrCC([O:59][CH3:60])=O.[C:61](=[O:64])([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:14]=[C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]2=[C:11]2[C:7]=1[C:8]([C:61](=[O:64])[C:60]([NH2:35])=[O:59])=[C:9]([CH3:26])[N:10]2[CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

8

Reactant 5

HCID 10796Cesium carbonateHCID 25134Boron tribromideHCID 60984Methyl bromoacetateHCID 11349089HCID 11349089, compoundHCID 11415570HCID 11415570, compound

Product 1

HCID 10274713HCID 10274713, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Preparation of 2-[(1-cyclohexylmethyl-2-methyl-1H-benz[g]indol-4-yl)oxy]acetic acid methyl ester. A solution of 1-cyclohexylmethyl-2-methyl-4-methoxybenz[g]indole (0.46 g, 1.5 mmol) in methylene chloride (14 mL) was cooled to 0° C. and treated with boron tribromide (0.35 mL, 3.7 mmol) in portions over 5 min. The mixture was allowed to warm to room temperature and stirred for 1 h. The mixture was poured onto ice and water and the resulting solution extracted with chloroform. The organic layer was washed once with water, once with dilute sodium bicarbonate solution, once with saturated sodium chloride solution, dried (sodium sulfate), filtered, and concentrated in vacuo. The residue was dissolved in N,N-dimethylformamide (10 mL) and treated with methyl bromoacetate (0.17 mL, 1.8 mmol) and cesium carbonate (0.64 g, 1.8 mmol) at room temperature with stirring for 29 h. The mixture was diluted with water and extracted three times with ethyl acetate. The combined ethyl acetate fractions were 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) of the residue provided 0.23 g (42%) of the title compound as a white fibrous solid: mp 156-158° C. 1H NMR (CDCl3) δ8.11 (d, J=8.4 Hz, 1H), 7.79 (d, J=8.1 Hz, 1H), 7.42 (t, J=6.6 Hz, 1H), 7.33 (t, J=7.0 Hz, 1H), 6.66 (s, 1H), 6.58 (s, 1H), 4.87 (s, 2H), 4.27 (d, J=7.3 Hz, 2H), 3.82 (s, 3H), 2.49 (s, 3H), 2.05 (bs, 1H), 1.68 (m, 5H), 1.12 (m, 5H); MS ES+ m/e 366 (p+1); IR (KBr, cm−1) 2928, 1757, 1210.

Workup

  1. extractionthe resulting solution extracted with chloroform
  2. washThe organic layer was washed once with water, once with dilute sodium bicarbonate solution, once with saturated sodium chloride 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. stirringwith stirring for 29 h
  8. extractionextracted three times with ethyl acetate
  9. washThe combined ethyl acetate fractions were 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-106028097d694940b0af775917ec6541
Source dataset
uspto-grants-2005_07
Patent number
US06916840B2

Reaction notes

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