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Benzyl Bromide → 3,3-Dibenzyl-5-(3,4,5-trimethoxy-phenyl)-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one

HRID 85048
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HRID 85048 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:14]=[C:15]3[CH2:21][C:20](=[O:22])[NH:19][C:16]3=[N:17][CH:18]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].CN(CCN(C)C)C.[Li][CH2:32][CH2:33][CH2:34][CH3:35].[CH2:36](Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[CH2:44]1[CH2:48]OC[CH2:45]1>>[CH2:35]([C:21]1([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:15]2[C:16](=[N:17][CH:18]=[C:13]([C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:14]=2)[NH:19][C:20]1=[O:22])[C:34]1[CH:48]=[CH:44][CH:45]=[CH:32][CH:33]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 7498Benzyl BromideHCID 8028Tetrahydrofuran2회HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 667786575-(3,4,5-Trimethoxy-phenyl)-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-oneHCID 178418339Butyllithium

생성물 1

HCID 462360463,3-Dibenzyl-5-(3,4,5-trimethoxy-phenyl)-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one
수율 38%

실험 절차

5-(3,4,5-Trimethoxy-phenyl)-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (95 mg, 0.316 mmol) and TMEDA (96 μl, 0.623 mmol) were dissolved in anhydrous THF (4 ml) and cooled to −78° C. n-BuLi (1.6 M in hexanes, 415 μl, 0.664 mmol) was added dropwise. After completed addition stirring was continued for 1 hr at −78° C. Benzyl bromide (41.3 μl, 0.348 mmol) was added dropwise as a 10% solution in anh. THF. After completed addition the reaction was allowed to warm up to room temperature while stirring overnight. The reaction was quenched by the addition of MeOH, evaporated and partitioned between water and DCM. Silica gel chromatography eluting with 0-50% EtOAc:Hexanes yielded the title compound (47 mg, 38%).

후처리

  1. additionwas added dropwise
  2. additionaddition
  3. additionaddition the reaction
  4. stirringwhile stirring overnight
  5. customThe reaction was quenched by the addition of MeOH
  6. customevaporated
  7. custompartitioned between water and DCM
  8. washSilica gel chromatography eluting with 0-50% EtOAc

출처 및 근거

ORD 기록
ord-1a77e20fae7b4a1c8b604bd6921383f8
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846909B2

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