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

HRID 917022ノート

反応式

HRID 917022 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

Sodium azide (1.51 g, 23.2 mmol) was added to a mixture 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%).

後処理

  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

出典と根拠

ORDレコード
ord-0c1af25135484eaaba703bff354359af
出典データセット
uspto-grants-2007_09
特許番号
US07271178B2

反応ノート

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