Bicarbonate Ion → Benzenamine, 2-bromo-4-(4-morpholinyl)-6-(trifluoromethyl)-

HRID 1158675노트

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HRID 1158675 반응식
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:3]=1[NH2:13].Br[CH2:15][CH2:16][O:17][CH2:18][CH2:19]Br.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:3]=1[NH2:13]

참가 물질

6

반응물 4

HCID 769Bicarbonate IonHCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 674076781,4-Benzenediamine, 2-bromo-6-(trifluoromethyl)-

생성물 1

HCID 67405904Benzenamine, 2-bromo-4-(4-morpholinyl)-6-(trifluoromethyl)-수율 63%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
180 °C

실험 절차

2-Bromo-6-trifluoromethyl-benzene-1,4-diamine (2.21 g), bis-(2-bromoethyl)ether (1.30 mL) and N,N-diisopropyl-ethylamine (4.64 mL) were mixed in N,N-dimethylformamide (19 mL) and heated to 180° C. for 30 minutes in a sealed microwave process vial. Saturated aqueous bicarbonate (100 mL) was added and the crude mixture was extracted with ethyl acetate (100 mL). The organic phase was washed with water (100 mL) and brine (100 mL), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to furnish 1.78 g (63%) of the title compound as a yellow solid. LC-MS (m/z) 326 (MH+); tR=2.54, (UV, ELSD) 83%, 75%. NMR (500 MHz, DMSO-d6): 2.99 (m, 4H), 3.70 (m, 4H), 5.00 (s, 2H), 7.00 (d, 1H), 7.38 (d, 1H).

후처리

  1. extractionthe crude mixture was extracted with ethyl acetate (100 mL)
  2. washThe organic phase was washed with water (100 mL) and brine (100 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-1bb7aae524484013bdd5752ed1634098
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812023B2

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