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

HRID 558210ノート

反応式

HRID 558210 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-244bc66615d440e7a49439f444af004f
出典データセット
uspto-grants-2011_11
特許番号
US08063049B2

反応ノート

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