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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
ノート
印刷プレビュー

反応式

HRID 333172 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 7498Benzyl BromideHCID 8028Tetrahydrofuran2 回HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 667786575-(3,4,5-Trimethoxy-phenyl)-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-oneHCID 178418339Butyllithium

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-87b55b7faaf147d0b15ad63d5da067de
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08877772B2

反応ノート

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