Cesium fluoride → 4-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)phenol

HRID 500816Notes

Reaction equation

Br[C:2]1[S:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[F:21])[CH:3]=1.[OH:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.[F-].[Cs+].C(=O)(O)[O-].[Na+]>COCCOC.O>[F:21][C:13]1[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=1[O:11][C:8]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:3]=[C:2]([C:26]3[CH:27]=[CH:28][C:23]([OH:22])=[CH:24][CH:25]=3)[S:10][C:9]=12

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-bromo-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine (42, scheme 8) (650 mg, 1.76 mmol) in ethylene glycol dimethyl ether (18 mL) were added 4-hydroxyphenylboronic acid (486 mg, 3.52 mmol), tetrakis-triphenylphosphine palladium(0) (203 mg, 0.18 mmol), cesium fluoride (802 mg, 5.28 mmol) and a solution of sodium bicarbonate (444 mg, 5.28 mmol) in water (1 mL). The reaction mixture was purged with nitrogen, heated at 80° C. for 4 hours, quenched with saturated aqueous ammonium chloride and extracted with EtOAc. The extract was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by trituration with methanol and ether to afford title compound 153 (418 mg, 62% yield) as a yellow solid. LRMS (M+1) 383.1 (100%).

Workup

customThe reaction mixture was purged with nitrogen
customquenched with saturated aqueous ammonium chloride
extractionextracted with EtOAc
washThe extract was washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customevaporated under reduced pressure
customThe residue was purified by trituration with methanol and ether

Sources & evidence

ORD record: ord-ea3cad13ed5a44ef92ad644c61cfe33d
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772247B2

Reaction notes

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