Water → 1-(4-Methoxybenzyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

HRID 40720

反応式

HRID 40720 の反応式
[H-].[Na+].C[O:4][C:5]([C:7]1[CH:8]=[C:9]2[CH:15]=[CH:14][NH:13][C:10]2=[N:11][CH:12]=1)=[O:6].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][CH:19]=1.O>CN(C=O)C>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:13]2[C:10]3=[N:11][CH:12]=[C:7]([C:5]([OH:4])=[O:6])[CH:8]=[C:9]3[CH:15]=[CH:14]2)=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1650214-Methoxybenzyl bromideHCID 22832049methyl 1H-pyrrolo[2,3-b]pyridine-5-carboxylate

生成物 1

HCID 582201621-(4-Methoxybenzyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid収率 25.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a stirred cooled 0° C. suspension of NaH (272 mg, 6.81 mmol) in DMF (23 mL) was added 1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid methyl ester (400 mg, 2.27 mmol). After 5 min, PMBBr (548 mg, 2.72 mmol) and KI (377 mg, 2.27 mmol) were added and the reaction mixture was allowed to warm to room temperature and stirring was continued overnight. The following day, water was added to quench the remaining Nail and the aqueous mixture was washed with EtOAc, which was discarded. The aqueous phase was collected and carefully acidified (pH ˜3) before extraction with EtOAc. The combined organics were dried and evaporated to afford 1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (160 mg, 0.57 mmol, 25% yield). ES MS (M+H+)=283.

後処理

  1. temperatureto warm to room temperature
  2. waitwas continued overnight
  3. customto quench the remaining Nail
  4. washthe aqueous mixture was washed with EtOAc, which
  5. customThe aqueous phase was collected
  6. extractionbefore extraction with EtOAc
  7. customThe combined organics were dried
  8. customevaporated

出典と根拠

ORDレコード
ord-7decd16c2ab94af9ac129939d6ac8506
出典データセット
uspto-grants-2013_09
特許番号
US08530483B2

関連ノート

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