Ethyl Acetate → Methyl 6-amino-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate

HRID 558210노트

반응식

HRID 558210 반응식
[N:1]([C:4]1[C:13]([Cl:14])=[C:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=2[Cl:23])[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=1)=[N+]=[N-].CCOC(C)=O>C(Cl)Cl.CC(O)=O.[Zn]>[NH2:1][C:4]1[C:13]([Cl:14])=[C:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=2[Cl:23])[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=1

참가 물질

6

반응물 2

HCID 8857Ethyl AcetateHCID 59519382Methyl 6-azido-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate

생성물 1

HCID 59519500Methyl 6-amino-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

To a suspension of methyl 6-azido-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate (316 mg, 0.76 mmol) in a mixture of DCM (6 ml) and AcOH (2 ml) was added Zn dust (255 mg, 3.9 mmol) in small portions. After complete addition it was furthers stirred at room temperature for 30 min. Then, the mixture was poured into EtOAc (30 ml), washed with H2O, saturated sodium bicarbonate solution and brine. The organic fractions were dried with Na2SO4 and the solvents were removed and the product was dried in oil-pump vacuo (246 mg, 83%). Rf (CHCl3/MeOH 30:1)=0.3. 1H-NMR (500 MHz, DMSO-D6): δ=9.17 (s, 1H), 8.45 (s, 1H), 7.70-7.70 (d, 1H), 7.38-7.36 (dd, 1H), 7.1 (s, 1H, br), 6.68-6.67 (d, 1H), 3.76 (s, 3H).

후처리

  1. additionAfter complete addition it
  2. washwashed with H2O, saturated sodium bicarbonate solution and brine
  3. dry with materialThe organic fractions were dried with Na2SO4
  4. customthe solvents were removed
  5. customthe product was dried in oil-pump vacuo (246 mg, 83%)

출처 및 근거

ORD 기록
ord-244bc66615d440e7a49439f444af004f
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063049B2

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