2-Fluoro-4-nitrophenol → (7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)(pyrrolidin-1-yl)methanone

HRID 418581

Reaction equation

HRID 418581 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[O:12])[S:10][C:3]=12.C([O-])([O-])=O.[K+].[K+].[F:24][C:25]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:26]=1[OH:34].CO.CCOC(C)=O>C1(OC2C=CC=CC=2)C=CC=CC=1>[F:24][C:25]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:26]=1[O:34][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[O:12])[S:10][C:3]=12

Participants

6

Reactant 4

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 11173165(7-Chlorothieno[3,2-b]pyridin-2-yl)(pyrrolidin-1-yl)methanoneHCID 21584119Ethylacetate methanol

Product 1

HCID 59424552(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)(pyrrolidin-1-yl)methanoneYield 93.8%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A mixture of 21 (2.4 g, 8.89 mmol), K2CO3 (4.97 g, 35.96 mmol) and 2-fluoro-4-nitrophenol (1.55 g, 9.89 mmol) were heated at 150° C. in diphenyl ether (40 mL) for 2 days. The mixture was purified by column chromatography (eluents EtOAc-hexane 5:95, 2:8, then MeOH-EtOAc 2:98, 5:95) to give the title compound 22 as a yellow solid (3.23 g, 93% yield). MS (m/z): 388.2 (M+H).

Workup

  1. customThe mixture was purified by column chromatography (eluents EtOAc-hexane 5:95, 2:8

Sources & evidence

ORD record
ord-d1ad1ee9b6cc4e188c9675a3c363d9cd
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Linked notes

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