2-Fluoro-4-nitrophenol → 2-(5-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazol-2-yl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

HRID 84360

Reaction equation

HRID 84360 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[N:11]([CH3:12])[C:10]([C:13]2[S:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3Cl)[CH:14]=2)=[N:9][CH:8]=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].C([O-])(O)=O.[Na+]>O(C1C=CC=CC=1)C1C=CC=CC=1.C(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[N:11]([CH3:12])[C:10]([C:13]2[S:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[O:33][C:25]3[CH:26]=[CH:27][C:28]([N+:30]([O-:32])=[O:31])=[CH:29][C:24]=3[F:23])[CH:14]=2)=[N:9][CH:8]=1

Participants

6

Reactant 3

HCID 98252-Fluoro-4-nitrophenolHCID 516892Sodium BicarbonateHCID 579194992-(5-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazol-2-yl)-7-chlorothieno[3,2-b]pyridine

Product 1

HCID 579195272-(5-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazol-2-yl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridineYield 31.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7583Diphenyl EtherSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 40 (5.9 g, 17.57 mmol), 2-fluoro-4-nitrophenol (5.52 g, 35.1 mmol) and NaHCO3 (1.346 g, 16.02 mmol) in Ph2O (7 mL) was heated to 180° C. for 4 hours. The reaction mixture was cooled to RT and diluted with DCM, filtered and concentrated. Purification of the residue by column chromatography (eluent EtOAc) afforded 41 (2.5 g, 31% yield) as a yellow solid. MS (m/z): 457.1 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification of the residue by column chromatography (eluent EtOAc)

Sources & evidence

ORD record
ord-e1a7d28874144d41bdc7e97b26018276
Source dataset
uspto-grants-2014_09
Patent number
US08846927B2

Linked notes

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