Acetic acid methylene chloride → Methyl 6-amino-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate

HRID 494701노트

반응식

HRID 494701 반응식
[CH3:1][O:2][C:3](=[O:23])[C:4]1[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:12]=2[Cl:18])=[C:8]([Cl:19])[C:7]([N:20]=[N+]=[N-])=[N:6][CH:5]=1.ClCCl.C(O)(=O)C>[Zn].C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:23])[C:4]1[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:12]=2[Cl:18])=[C:8]([Cl:19])[C:7]([NH2:20])=[N:6][CH:5]=1

참가 물질

5

반응물 2

HCID 21922555Acetic acid methylene chlorideHCID 59519382Methyl 6-azido-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate

생성물 1

HCID 59519500Methyl 6-amino-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate수율 98%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 8857Ethyl Acetate용매

실험 절차

Zinc powder (10 g, 155 mmol) was added portionwise to a suspension of 6-azido-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinic acid methyl ester (27) (12.94 g, 31 mmol) in 3:1 dichloromethane/acetic acid (300 mL). After fifteen minutes the reaction mixture was poured into 700 mL ethyl acetate, washed with water, saturated sodium bicarbonate and brine. The organic solution was dried over NaSO4, filtered, and concentrated in vacuo to provide the desired product (28) as an off-white solid (11.85 g, 98%). MS (APCI+) m/z 390, 392, 394 (M+; Cl, Br pattern) detected.

후처리

  1. washwashed with water, saturated sodium bicarbonate and brine
  2. dry with materialThe organic solution was dried over NaSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-48793d9a77984ef486ed13941ca4b84f
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538120B2

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