2-Amino-5-fluoro-N-methoxy-N-methylbenzamide → (2-Amino-5-fluorophenyl)(phenyl)methanone

HRID 19676

반응식

HRID 19676 반응식
[NH2:1][C:2]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:3]=1[C:4](N(OC)C)=[O:5].[C:15]1([Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1.C(Cl)Cl>[NH2:1][C:2]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:3]=1[C:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:5]

참가 물질

5

반응물 2

HCID 534075722-Amino-5-fluoro-N-methoxy-N-methylbenzamideHCID 178418255HCID 178418255, 화합물2회

생성물 1

HCID 778082(2-Amino-5-fluorophenyl)(phenyl)methanone

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-78 °C

실험 절차

To a −78° C. solution of 2-amino-5-fluoro-N-methoxy-N-methylbenzamide in THF (100 mL) was added 1M phenylmagnesium bromide in THF (124.12 mL, 124.12 mmol). The reaction was stirred from −78° C. to ambient temperature over 3.5 h and then cooled again to −78° C. Additional 1M phenylmagnesium bromide in THF (62.06 mL, 62.06 mmol) was added and the reaction stirred at −78° C. for another hour. The reaction was then diluted with CH2Cl2 (500 mL) and quenched with saturated ammonium chloride solution (300 mL). The layers were separated and the organic one washed with brine (300 mL), dried over Na2SO4, filtered and concentrated in vacuo. Purification by normal phase chromatography (3-8% MeOH/CH2Cl2) yielded (2-amino-5-fluorophenyl)(phenyl)methanone as a yellow solid. 1H NMR (CDCl3, 400 MHz) 7.63 (m, 2H, ArH); 7.55 (m, 1H, ArH); 7.47 (m, 2H, ArH); 7.15 (m, 1H, ArH); 7.08 (m, 1H, ArH); 6.70 (m, 1H, ArH); 5.91 (s, NH2); MS (Electrospray): m/z 216.1 (M+H).

후처리

  1. stirringthe reaction stirred at −78° C. for another hour
  2. customquenched with saturated ammonium chloride solution (300 mL)
  3. customThe layers were separated
  4. washthe organic one washed with brine (300 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by normal phase chromatography (3-8% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-ab87011a7b994501bcc359bba50fa0ce
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745452B2

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