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Triethylamine → 1-Benzyl-2,3-dibromo-4-(2,2-dimethyl-propionyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642244
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HRID 642244 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:24])=[C:8]2[C:14]([Br:15])=[C:13]([Br:16])[N:12]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[C:32](Cl)(=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34]>CN(C1C=CN=CC=1)C.ClCCl.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:24][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[C:8]2[C:14]([Br:15])=[C:13]([Br:16])[N:12]([CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]
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참가 물질

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반응물 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 684285581-benzyl-2,3-dibromo-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

생성물 1

HCID 684292361-Benzyl-2,3-dibromo-4-(2,2-dimethyl-propionyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester수율 85.2%

시약·촉매·용매 3

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 6344Dichloromethane용매
HCID 8857Ethyl Acetate용매

실험 절차

To a stirring mixture of 1-benzyl-2,3-dibromo-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (492 mg, 1.08 mmol), triethylamine (300 μL, 2.16 mmol), and DMAP (13 mg, 0.11 mmol) in anhydrous dichloromethane (5 mL) was added pivaloyl chloride (160 μL, 1.30 mmol); the mixture was stirred for 1 h at room temperature before diluted with EtOAc, then washed with diluted HCl aqueous solution, saturated NaCl aqueous solution respectively; the EtOAc phase was dried over anhydrous sodium sulfate, concentrated, the residue was purified by column to give a foamy brown solid, the desired title compound (495 mg, 85%). The title compound, ESI MS (m/z): 537 (M+H+).

후처리

  1. washwashed with diluted HCl aqueous solution, saturated NaCl aqueous solution respectively
  2. dry with materialthe EtOAc phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customthe residue was purified by column
  5. customto give a foamy brown solid

출처 및 근거

ORD 기록
ord-542870c307504b19ab1e72a349df6dbd
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07696223B2

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