Indole-2-carboxylic acid → HCID 22676754、化合物

HRID 1006246ノート

反応式

HRID 1006246 の反応式
N1[C:9]2[C:4](=[CH:5]C=CC=2)[CH:3]=C1C(O)=O.[Br:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15]=1[C:23]([OH:25])=[O:24].C(OC(OC(C)(C)C)N(C)C)(C)(C)C>C1(C)C=CC=CC=1>[Br:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15]=1[C:23]([O:25][C:4]([CH3:9])([CH3:5])[CH3:3])=[O:24]

参加物

5

反応物 3

HCID 72899Indole-2-carboxylic acidHCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 23256883-bromo-1H-indole-2-carboxylic acid

生成物 1

HCID 22676754HCID 22676754、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

Indole-2-carboxylic acid was converted to 3-bromoindole-2-carboxylic acid using the method described for Example 13. N,N-dimethylformamide di-tert-butyl acetal (35 mL) was added dropwise to a stirring mixture of indole-3-bromo-2-carboxylic acid (14.9 g, 62 mmol) suspended in toluene (100 mL). After the addition was complete, the reaction was heated at 90° C. for 8 h. The reaction mixture was then cooled to room temperature and washed with cold water (2×100 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield the crude tert-butyl 3-bromoindole-2-carboxylate, assume quantitative yield. The crude product was used in the next step without purification.

後処理

  1. additionAfter the addition
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. washwashed with cold water (2×100 mL)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-86bb1b1400ff4981bb031d4cedf85771
出典データセット
uspto-grants-2004_09
特許番号
US06787651B2

反応ノート

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