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

HRID 2108754노트

반응식

HRID 2108754 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a2454307d0784adb8946134a70311ebe
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514448B2

반응 노트

불러오는 중…