Dabco → 4-(2-Fluoro-4-nitrophenoxy)-6-(2-morpholinopyridin-4-yl)pyrrolo[2,1-f][1,2,4]triazine

HRID 2117178Notes

Reaction equation

HRID 2117178 reaction equation
Cl[C:2]1[C:7]2=[CH:8][C:9]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[CH:12]=3)=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[F:23][C:24]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:26][C:25]=1[OH:33].C1N2CCN(CC2)C1>CC#N>[F:23][C:24]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:26][C:25]=1[O:33][C:2]1[C:7]2=[CH:8][C:9]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[CH:12]=3)=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 98252-Fluoro-4-nitrophenolHCID 210816804-Chloro-6-(2-morpholinopyridin-4-yl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 210816524-(2-Fluoro-4-nitrophenoxy)-6-(2-morpholinopyridin-4-yl)pyrrolo[2,1-f][1,2,4]triazineYield 33%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of the crude 4-chloro-6-(2-morpholinopyridin-4-yl)pyrrolo[2,1-f][1,2,4]triazine in MeCN (5 mL) were added 2-fluoro-4-nitrophenol (59 mg, 0.37 mmol) and DABCO (45 mg, 0.4 mmol). The reaction mixture was stirred at room temperature for 2 h. The solvent was removed in vacuo and the residue was purified by flash column chromatography (ISCO RediSep® silica gel cartridge) to give the desired compound (54 mg, 33% yield in two steps). MS(ESI) m/z 437.2 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash column chromatography (ISCO RediSep® silica gel cartridge)

Sources & evidence

ORD record
ord-584094a904ed4d208a6f75baee89e589
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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