Diphenyl Ether → (3-(tert-Butyldimethylsilyloxy)azetidin-1-yl)(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)methanone

HRID 418688Notes

Reaction equation

[Si:1]([O:8][CH:9]1[CH2:12][N:11]([C:13]([C:15]2[S:23][C:22]3[C:17](=[N:18][CH:19]=[CH:20][C:21]=3Cl)[CH:16]=2)=[O:14])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F:25][C:26]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:27]=1[OH:35].C([O-])([O-])=O.[K+].[K+].O(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl>[Si:1]([O:8][CH:9]1[CH2:12][N:11]([C:13]([C:15]2[S:23][C:22]3[C:17](=[N:18][CH:19]=[CH:20][C:21]=3[O:35][C:27]3[CH:28]=[CH:29][C:30]([N+:32]([O-:34])=[O:33])=[CH:31][C:26]=3[F:25])[CH:16]=2)=[O:14])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of (3-(tert-butyldimethylsilyloxy)azetidin-1-yl)(7-chlorothieno[3,2-b]pyridin-2-yl)methanone 272 (749.7 mg, 1.96 mmol) (WO 2006/010264), 2-fluoro-4-nitrophenol (461 mg, 2.94 mmol), K2CO3 (518 mg, 3.92 mmol) and Ph2O (2.6 mL) was stirred in a sealed tube for 1.5 h at 170° C. The mixture was diluted with DCM, extracted with water, the organic phase dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash chromatography (eluted successively with: EtOAc/hexanes 1:1, EtOAc, EtOAc/MeOH 4:1) affording 273 (336 mg, 0.67 mmol, 34% yield). MS (m/z): (M+1) 504.1 (100%).

Workup

extractionextracted with water
dry with materialthe organic phase dried over anhydrous Na2SO4
concentrationconcentrated
customThe residue was purified by flash chromatography (
washeluted successively with: EtOAc/hexanes 1:1, EtOAc, EtOAc/MeOH 4:1)

Sources & evidence

ORD record: ord-736aef52392d4a04838cae157cb93da2
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093264B2

Reaction notes

Loading…