Methyl 4-(bromomethyl)-3-methoxybenzoate → HCID 19870596, compound

HRID 330193Notes

Reaction equation

HRID 330193 reaction equation
[CH2:1]([NH:5][C:6](=[O:18])[CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:17])[CH:12]=[CH:11]2)[CH2:2][CH2:3][CH3:4].Br[CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[O:31][CH3:32]>CN(C)C=O>[CH2:1]([NH:5][C:6]([CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:17])[CH:12]=[C:11]2[CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[O:31][CH3:32])=[O:18])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoate2×HCID 54136909HCID 54136909, compound

Product 1

HCID 19870596HCID 19870596, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-butyl-1-methylindole-5-acetamide (0.46 g) and methyl 4-bromomethyl-3-methoxybenzoate (0.49 g) in dimethylformamide (10 ml) was heated at 80° under a nitrogen atmosphere for 18 hr. Additional methyl 4-bromomethyl-3-methoxybenzoate (0.49 g) was added to the reaction and stirring was continued for 18 hr at 80°. The dimethylformamide was evaporated: and the oily residue was purified by flash chromatography, eluting with 1:1 ethyl acetate:hexane to give methyl 4-(5-butylcarbamoylmethyl-1-methylindol-3-ylmethyl)-3-methoxybenzoate (0.23 g, 30%) as a white solid; NMR (250 MHz, CDCl3): 0.84(t, 3H, N(CH2)CH3), 1.35-1.16(m, 4H, NCH2 (CH2)2), 3.13(q, 2H, NCH2), 3.65(s, 2H, ArCH2CO), 3.75(s, 3H, NCH3), 3.90(s, 3H, OCH3), 3.94(s, 3H, OCH3), 4.09(s, 2H, ArCH2Ar'), 5.34(br, 1H, NH).

Workup

  1. customThe dimethylformamide was evaporated
  2. customthe oily residue was purified by flash chromatography
  3. washeluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-63c9d07fe3314235ab25a0de18fc3272
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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