Tetrahydrofuran → 7-Methoxy-4-((5-phenyl-[1,2,3]triazolo[1,5-a]pyridin-3-yl)methoxy)quinoline

HRID 1511284ノート

反応式

HRID 1511284 の反応式
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]3[N:13]=[N:14][C:15]([CH2:16][OH:17])=[C:9]3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[AlH4-].[Li+].C1([C:26]2[CH:31]=[CH:30][N:29]3N=N[C:34]([C:35]([O:37][CH3:38])=O)=[C:28]3[CH:27]=2)C=CC=CC=1.[CH2:39]1COC[CH2:40]1>CCOC(C)=O>[CH3:38][O:37][C:35]1[CH:34]=[C:28]2[C:27]([C:26]([O:17][CH2:16][C:15]3[N:14]=[N:13][N:10]4[CH:11]=[CH:12][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[CH:8][C:9]=34)=[CH:31][CH:30]=[N:29]2)=[CH:40][CH:39]=1

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 28112Lithium aluminum hydrideHCID 67502437Methyl 5-phenyl-[1,2,3]triazolo[1,5-a]pyridine-3-carboxylateHCID 67502444(5-Phenyl-[1,2,3]triazolo[1,5-a]pyridin-3-yl)methanol

生成物 1

HCID 576913407-Methoxy-4-((5-phenyl-[1,2,3]triazolo[1,5-a]pyridin-3-yl)methoxy)quinoline

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

(5-Phenyl-[1,2,3]triazolo[1,5-a]pyridin-3-yl)methanol To a cooled (ice bath) suspension of lithium tetrahydroaluminate (0.0929 g, 2.45 mmol) in 2 mL THF (anhy) was added slowly a solution of methyl 5-phenyl-[1,2,3]triazolo[1,5-a]pyridine-3-carboxylate (0.310 g, 1.22 mmol) in 20 mL THF (internal temp remained <20 C). The mixture was allowed to stir in the ice bath 10 minutes. The mixture was diluted with EtOAc, washed with water, sat. NaHCO3, the organic layer dried over Na2SO4, and filtered. The aqueous layer still had uv activity so a solution of Rochelle's salt and EA were added and the mixture stirred 30 min. The organic layer was washed with sat NaHCO3, dried over Na2SO4, filtered, combined with main portion and evaporated. The title compound was isolated as a yellow solid.

後処理

  1. washwashed with water, sat. NaHCO3
  2. dry with materialthe organic layer dried over Na2SO4
  3. filtrationfiltered
  4. additionwere added
  5. washThe organic layer was washed with sat NaHCO3
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-bc1bda0c9b3e4281bd36918c2ea86459
出典データセット
uspto-grants-2012_07
特許番号
US08212041B2

反応ノート

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