Potassium Phosphate, Tribasic → 2-(2'-Fluoro-3-methyl-2,4'-bipyridin-5-yl)acetic acid

HRID 592217Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[CH3:12].[F:13][C:14]1[CH:19]=[C:18](B(O)O)[CH:17]=[CH:16][N:15]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2].CS(C)=O>[F:13][C:14]1[CH:19]=[C:18]([C:2]2[C:3]([CH3:12])=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][N:7]=2)[CH:17]=[CH:16][N:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a reaction vial was added 2-(6-chloro-5-methylpyridin-3-yl)acetic acid 74-4 (185 mg, 1 mmol), 2-fluoropyridin-4-ylboronic acid 193-1 (220 mg, 1.5 mmol), Pd(OAc)2 (12 mg, 0.05 mmol), S-Phos (41 mg, 0.1 mmol) and K3PO4 (636 mg, 3 mmol) in 1 mL 2-butanol. The reaction was heated to 100° C. and stirred for 2 hours. The reaction was cooled down to room temperature and then diluted to DMSO. The reaction mixture was filtered and the filtrate was purified by reverse-phase HPLC to give 2-(2′-fluoro-3-methyl-2,4′-bipyridin-5-yl)acetic acid 193-2 as white solid. MS m/z 247.2 (M+1).

Workup

temperatureThe reaction was cooled down to room temperature
filtrationThe reaction mixture was filtered
customthe filtrate was purified by reverse-phase HPLC

Sources & evidence

ORD record: ord-936fab4025584279a7269a8688b5ec03
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238646B2

Reaction notes

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