Cesium carbonate → HCID 87788430, compound

HRID 895936Notes

Reaction equation

HRID 895936 reaction equation
[CH3:1][O:2][C:3](=[O:28])[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]([CH2:26][CH3:27])[N:10]2[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([N:36]1C2C(=C(OC)C=C3C=CC=CC3=2)C=C1CC)C1C=CC=CC=1.B(Br)(Br)Br.[C:57](=[O:60])([O-])[O-].[Cs+].[Cs+].BrCC([O:67][CH3:68])=O>C(Cl)(Cl)Cl.CN(C)C=O.O.C(OCC)(=O)C>[OH2:2].[CH3:1][O:2][C:3](=[O:28])[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:57](=[O:60])[C:68]([NH2:36])=[O:67])=[C:9]([CH2:26][CH3:27])[N:10]2[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH2:36][C:57](=[O:60])[C:68]([C:8]1[C:7]2[C:11](=[C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]3=[CH:14][C:6]=2[O:5][CH2:4][C:3]([O:2][CH3:1])=[O:28])[N:10]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9]=1[CH2:26][CH3:27])=[O:67]

Participants

10

Reactant 5

HCID 10796Cesium carbonateHCID 25134Boron tribromideHCID 60984Methyl bromoacetateHCID 20812274HCID 20812274, compoundHCID 22381010HCID 22381010, compound

Product 1

HCID 87788430HCID 87788430, compoundYield 74%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Preparation of 2-[(2-ethyl-1-benzyl-1H-benz[g]indol-4-yl)oxy]acetic acid methyl ester. A solution of 1-benzyl-2-ethyl-4-methoxybenz[g]indole (0.43 g, 1.4 mmol) in chloroform (8 mL) was cooled to 0° C. and treated with boron tribromide (0.36 mL, 3.8 mmol). The mixture was warmed to room temperature over 2 h, and poured into water. The mixture was extracted with fresh chloroform. The combined chloroform extracts were washed once with water, once with saturated sodium chloride solution, dried (sodium sulfate), filtered, and concentrated in vacuo to provide a highly colored solid. This material was added to a suspension of cesium carbonate (0.77 g, 2.4 mmol) in N,N-dimethylformamide (8 mL) and treated with methyl bromoacetate (0.23 mL, 2.4 mmol) at room temperature for 2 h. The mixture was diluted with water, and extracted twice with ethyl acetate. The combined ethyl acetate fractions were washed three times with water and once with saturated sodium chloride solution. The resulting solution was dried (sodium sulfate), filtered, and concentrated in vacuo to provide a red solid. Chromatography (silica gel, 20% ethyl acetate/80% hexane) provided 376 mg (74%) of the title compound as a white solid: mp 165-167° C. 1H NMR (CDCl3) δ7.95 (d, J=8.4 Hz, 1H), 7.75 (d, J=8.1 Hz, 1H), 7.28 (m, 4H), 7.16 (t, J=7.0 Hz, 1H), 7.05 (d, 6.6 Hz, 2H), 6.74 (s, 1H), 6.69 (s, 1H), 5.77 (s, 2H), 4.91 (s, 2H), 3.85 (s, 3H), 2.76 (q, J=8.4 Hz, 2H), 1.38 (t, J=7.3 Hz, 3H); MS ES+ m/e 374 (p+1).

Workup

  1. extractionThe mixture was extracted with fresh chloroform
  2. washThe combined chloroform extracts were 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 a highly colored solid
  7. extractionextracted twice with ethyl acetate
  8. washThe combined ethyl acetate fractions were washed three times with water
  9. dry with materialThe resulting solution was dried (sodium sulfate)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto provide a red solid

Sources & evidence

ORD record
ord-1a9debb1d2224e9cb2a29c5e5d3e4398
Source dataset
uspto-grants-2005_07
Patent number
US06916840B2

Reaction notes

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