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

HRID 40720

반응식

HRID 40720 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7decd16c2ab94af9ac129939d6ac8506
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530483B2

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