1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(3-Methoxybenzyl)-5-bromothiophene-3-carboxamide

HRID 2108754Notes

Reaction equation

HRID 2108754 reaction equation
[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][NH2:16].CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O>CN(C=O)C.CCOC(C)=O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][NH:16][C:7]([C:4]1[CH:3]=[C:2]([Br:1])[S:6][CH:5]=1)=[O:9]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 211563-MethoxybenzylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 120399785-Bromothiophene-3-carboxylic acid

Product 1

HCID 57421982N-(3-Methoxybenzyl)-5-bromothiophene-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Bromothiophene-3-carboxylic acid (70%) (200 mg, 0.6 mmol of monobromide) was dissolved in DMF with 3-methoxybenzyl amine (0.3 g, 2.2 mmol), EDCI (0.42 g, 2.2 mmol), and HOBt hydrate (0.06 g, 0.4 mmol). The reaction mixture was stirred at room temperature for 3 days, diluted with EtOAc and the organic layer washed with 10% citric acid, saturated sodium bicarbonate, and brine. The organic layer was then dried over sodium sulfate and concentrated to an oil, which was purified by column chromatography on silica (10 to 30 5 EtOAc/hexanes) to give the product as a colorless oil, 195 mg, 0.6 mmol, 100%. 1H NMR 500 MHz (CDCl3) 7.81 (1H, s), 7.35 (1H, s), 7.28 (1H, m), 6.93 (1H, m), 6.87 (2H, m), 6.23 (1H, br s), 4.57 (2H, d), 3.84 (3H, s).

Workup

  1. washthe organic layer washed with 10% citric acid, saturated sodium bicarbonate, and brine
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. concentrationconcentrated to an oil, which
  4. customwas purified by column chromatography on silica (10 to 30 5 EtOAc/hexanes)

Sources & evidence

ORD record
ord-a2454307d0784adb8946134a70311ebe
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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