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

HRID 2176495Notes

Reaction equation

HRID 2176495 reaction equation
[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

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(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.

Workup

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

Sources & evidence

ORD record
ord-1f22ebaa08ce4fd79c87480eb2f516b8
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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