Sodium Carbonate → 7-Fluoro-6-(2-fluoropyridin-3-yl)-2-phenylchroman-4-one

HRID 1408708Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[O:8][CH:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:6][C:5]2=[O:19].[F:20][C:21]1[C:26](B(O)O)=[CH:25][CH:24]=[CH:23][N:22]=1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CCO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:12][C:11]1[CH:10]=[C:9]2[C:4]([C:5](=[O:19])[CH2:6][CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:8]2)=[CH:3][C:2]=1[C:26]1[C:21]([F:20])=[N:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 6-bromo-7-fluoro-2-phenylchroman-4-one (318 mg, 0.994 mmol), 2-fluoropyridin-3-ylboronic acid (210 mg, 1.5 mmol), Na2CO3 (318 mg, 2.98 mmol), PPh3 (34 mg) and Pd(PPh3)2Cl2 (59 mg, 0.1 mmol) in toluene/EtOH (v/v=1/1, 10.5 mL) was degassed and stirred at 110° C. for 20 minutes. The reaction mixture was concentrated in vacuo to give the residue, which was purified by preparative TLC to give 7-fluoro-6-(2-fluoropyridin-3-yl)-2-phenylchroman-4-one (78 mg, 23%).

Workup

customwas degassed
concentrationThe reaction mixture was concentrated in vacuo
customto give the residue, which
customwas purified by preparative TLC

Sources & evidence

ORD record: ord-957b7d6e9dcf4e6d9d9cd34a56320cc5
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921359B2

Reaction notes

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