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

HRID 1867282노트

반응식

HRID 1867282 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

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 healed 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%. 1H 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-2cfd2cf31fb542559f55383a86019131
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07632835B2

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