Methanol → HCID 13037353, compound

HRID 1085450Notes

Reaction equation

HRID 1085450 reaction equation
[CH3:1][N:2]([CH3:5])[CH:3]=[O:4].C(OC([C:11]1[N:12]=[CH:13][C:14]2[NH:15][C:16]3[C:21]([C:22]=2[CH:23]=1)=[CH:20][C:19](Br)=[CH:18][CH:17]=3)=O)C.[Na].[CH3:26][OH:27]>[Cu]I>[CH3:1][N:2]([CH3:5])[C:3]([C:11]1[N:12]=[CH:13][C:14]2[NH:15][C:16]3[C:21]([C:22]=2[CH:23]=1)=[CH:20][C:19]([O:27][CH3:26])=[CH:18][CH:17]=3)=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 5360545SodiumHCID 13037312ethyl 6-bromo-9H-pyrido[3,4-b]indole-3-carboxylate

Product 1

HCID 13037353HCID 13037353, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
145 °C

Procedure

4 ml of dimethylformamide, 250 mg of copper (I) iodide and 160 mg of 6-bromo-β-carbolin-3-carboxylic acid ethyl ester are added to a solution, prepared under argon, of 230 mg of sodium in 3 ml of absolute methanol, and the whole is heated for 6 hours at 145° C. The solution is then concentrated in vacuo, the residue is washed with water, dried and chromatographed on silica gel with chloroform-methanol (8:2). 67 mg of 6-methoxy-β-carbolin-3-carboxylic acid dimethylamide of melting point 195° C. (decomposition) is obtained.

Workup

  1. concentrationThe solution is then concentrated in vacuo
  2. washthe residue is washed with water
  3. customdried
  4. customchromatographed on silica gel with chloroform-methanol (8:2)

Sources & evidence

ORD record
ord-aadcc3b8a5e8433c8edfeee83ecc9d33
Source dataset
uspto-grants-1991_04
Patent number
US05010077

Reaction notes

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