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4-(Bromomethyl)-1,2-dichlorobenzene → [1-(3,4-dichloro-benzyl)-1H-pyrrolo[2,3-b]pyridine-3-yl]acetic acid methyl ester

HRID 1445586
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HRID 1445586 반응식
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[Cl:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][C:41]=1[Cl:42])[CH2:37]Br>CN(C=O)C>[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:37][C:36]2[CH:39]=[CH:40][C:41]([Cl:42])=[C:34]([Cl:33])[CH:35]=2)[CH:6]=1
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참가 물질

5

반응물 3

HCID 6397264-(Bromomethyl)-1,2-dichlorobenzeneHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 25067325Methyl 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)acetate

생성물 1

HCID 67219084[1-(3,4-dichloro-benzyl)-1H-pyrrolo[2,3-b]pyridine-3-yl]acetic acid methyl ester

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

To an ice cold solution of (1H-pyrrolo[2,3-b]pyridine-3-yl)-acetic acid methyl ester (50 mg, 0.26 mmol) in DMF (1 mL), is added BEMP (0.122 mL, 0.42 mmol). The reaction mixture is stirred at ambient temperature for 40 minutes, then 3,4-dichlorobenzyl bromide (0.101 g, 0.42 mmol) is added and the reaction mixture is stirred for 16 hours at ambient temperature. The reaction mixture is poured into ice cold water (40 mL) and extracted with EtOAc, washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The crude product is purified by column chromatography on silica gel using a pre-packed Isolute™ silica column (2 g) eluting with 1:20 EtOAc/iso-hexane, furnishing [1-(3,4-dichloro-benzyl)-1H-pyrrolo[2,3-b]pyridine-3-yl]-acetic acid methyl ester; MH+=349.

후처리

  1. stirringthe reaction mixture is stirred for 16 hours at ambient temperature
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude product is purified by column chromatography on silica gel using a pre-packed Isolute™ silica column (2 g)
  8. washeluting with 1:20 EtOAc/iso-hexane

출처 및 근거

ORD 기록
ord-0c7da18fea4f4ec5b6c620a6974627b3
출처 데이터셋
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07666878B2

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