Potassium Carbonate → HCID 59026768, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[C:9]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[CH:8][N:7]=[CH:6][C:5]=1Br.[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3](=[O:19])[C:4]1[C:9]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[CH:8][N:7]=[CH:6][C:5]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[F:20]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
3-Bromo-5-(2-fluoro-phenylamino)-isonicotinic acid methyl ester (1.25 g, 3.84 mmol), 2-fluorophenylboronic acid (0.81 g, 5.77 mmol), Pd(OAc)2 (30 mg, 0.12 mmol), S-Phos (90 mg, 0.24 mmol), and K2CO3 (1.6 g, 11.5 mmol) were suspended in dioxane/H2O (9 mL, 9/1, v/v) and stirred overnight at 100° C. The reaction solution was diluted with EtOAc, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 0 to 50% EtOAc in hexanes to afford the desired product (680 mg, 52%) as a yellow solid. LC-MS (M+H=341, obsd.=341).
Workup
- filtrationfiltered through an Extrelut column
- washThe column was washed with EtOAc
- concentrationthe filtrate was concentrated
- customThe crude product was purified via Biotage
- washeluting with a gradient of 0 to 50% EtOAc in hexanes
Sources & evidence
- ORD record
- ord-5c43a465a56a4233acf17d96a244f14d
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08076486B2
Reaction notes
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