Sodium Azide → 6-Azido-4-(4-bromo-2-chlorophenylamino)nicotinic acid tert-butyl ester

HRID 494711노트

반응식

HRID 494711 반응식
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([O:9][C:10](=[O:27])[C:11]1[C:16]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=2[Cl:25])=[CH:15][C:14](Cl)=[N:13][CH:12]=1)([CH3:8])([CH3:7])[CH3:6]>CN(C=O)C.CCOC(C)=O>[C:5]([O:9][C:10](=[O:27])[C:11]1[C:16]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=2[Cl:25])=[CH:15][C:14]([N:1]=[N+:2]=[N-:3])=[N:13][CH:12]=1)([CH3:8])([CH3:6])[CH3:7]

참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 865967784-(4-Bromo-2-chlorophenylamino)-6-chloronicotinic acid tert-butyl ester

생성물 1

HCID 865967796-Azido-4-(4-bromo-2-chlorophenylamino)nicotinic acid tert-butyl ester수율 43%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

Sodium azide (1.51 g, 23.2 mmol) was added to a suspension of 4-(4-bromo-2-chlorophenylamino)-6-chloronicotinic acid tert-butyl ester (40) (3.23 g, 7.73 mmol) in DMF (60 mL). The reaction mixture was heated to 80° C. and stirred for 16 hours. After cooling to room temperature, the reaction was diluted with EtOAc and washed with water, saturated NaHCO3 and brine. The organic layer was dried (Na2SO4) and concentrated. Purification by flash column chromatography using the Biotage system (CH2Cl2) (repeated) provided the desired product (41) (1.41 g, 43%).

후처리

  1. temperatureAfter cooling to room temperature
  2. washwashed with water, saturated NaHCO3 and brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by flash column chromatography

출처 및 근거

ORD 기록
ord-92f24da971fd48c0aa2e829f42208fbe
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538120B2

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