Water → Ethyl 3-(5-(2-((2',4'-dichloro-[1,1'-biphenyl]-4-yl)carbamoyl)-4,5-difluorophenyl)picolinamido)propanoate
Reaction equation
Br[C:2]1[CH:24]=[C:23]([F:25])[C:22]([F:26])=[CH:21][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])=[CH:9][CH:8]=1)=[O:5].CC1(C)C(C)(C)OB([C:35]2[CH:36]=[CH:37][C:38]([C:41]([NH:43][CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])=[O:42])=[N:39][CH:40]=2)O1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[C:10]1[CH:11]=[CH:12][C:7]([NH:6][C:4]([C:3]2[CH:21]=[C:22]([F:26])[C:23]([F:25])=[CH:24][C:2]=2[C:35]2[CH:36]=[CH:37][C:38]([C:41]([NH:43][CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])=[O:42])=[N:39][CH:40]=2)=[O:5])=[CH:8][CH:9]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
2-Bromo-N-(2′,4′-dichloro-[1,1′-biphenyl]-4-yl)-4,5-difluorobenzamide (100 mg, 0.22 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate (114 mg, 0.33 mmol), Pd(dppf)Cl2 (24 mg, 0.03 mmol), and K2CO3 (60 mg, 0.44 mmol) were dissolved in 1,4-dioxane (1 mL) and water (0.5 mL) and the resulting mixture was heated to 85° C. After 2 h the resulting mixture directly purified via column chromatography to yield the title compound.
Workup
- customAfter 2 h the resulting mixture directly purified via column chromatography
Sources & evidence
- ORD record
- ord-c8b76a416a1a4739b67ca117f2515f2d
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748624B2
Reaction notes
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