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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 333172
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HRID 333172 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
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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%). 1H NMR (CDCl3, 300 MHz): δ 8.83 (s, 1H), 8.18 (d, J=1.2 Hz, 1H), 7.19 (d, J=1.2 Hz, 1H), 7.14 (m, 6H), 6.99 (m, 4H), 6.61 (s, 2H), 3.96 (s, 6H), 3.90 (s, 3H), 3.30 (d, J=8.0 Hz, 2H), 3.26 (d, J=8.0 Hz, 2H).

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-87b55b7faaf147d0b15ad63d5da067de
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08877772B2

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