Ethanol → 8-Ethyl-thienyl[3',4':6,5]dipyrido[2,3-b:3',2'-f]azepine

HRID 580817Notes

Reaction equation

HRID 580817 reaction equation
F[C:2]1[C:7]([C:8]2[C:12]([C:13]3[C:14]([NH:19][CH2:20][CH3:21])=[N:15][CH:16]=[CH:17][CH:18]=3)=[CH:11][S:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C(O)C>O1CCCC1.C(OCC)(=O)C>[CH3:21][CH2:20][N:19]1[C:14]2[N:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12]2[C:8](=[CH:9][S:10][CH:11]=2)[C:7]2[CH:6]=[CH:5][CH:4]=[N:3][C:2]1=2

Participants

6

Reactant 3

HCID 702EthanolHCID 3251421Potassium bis(trimethylsilyl)amideHCID 154085633-(2-Fluoropyridin-3-yl)-4-(2-ethylaminopyridin-3-yl)thiophene

Product 1

HCID 4746208-Ethyl-thienyl[3',4':6,5]dipyrido[2,3-b:3',2'-f]azepine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(2-fluoropyridin-3-yl)-4-(2-ethylaminopyridin-3-yl)thiophene (0.021 g) in tetrahydrofuran (1.5 mL was added potassium bistrimethylsilylamide (0.5M in toluene) until no yellow color appeared on addition of further reagent. The mixture was stirred for 5 minutes, ethanol was added, the mixture was diluted with ethyl acetate, washed with water, dried, filtered and evaporated. The residue was fractionated by chromatography to give 8-ethyl-thienyl[3',4':6,5]dipyrido[2,3-b:3',2'-f]azepine mp 140-142° C.

Workup

  1. additionappeared on addition of further reagent
  2. washwashed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-c63a9319e1304d65a6de669ff8c2c96d
Source dataset
uspto-grants-1999_07
Patent number
US05919779

Reaction notes

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