Dimethylformamide → HCID 10288404, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:16](CC#N)[C@H:17]([C:22]([NH2:24])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])=[CH:4][CH:3]=1.[N:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.[C:37]([O-])([O-])=O.[Na+].[Na+].C[N:44]([CH:46]=O)C>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]>[C:46]([CH2:37][NH:24][C:22](=[O:23])[C@H:17]([CH2:18][CH:19]([CH3:20])[CH3:21])[NH:16][C@@H:8]([C:5]1[CH:6]=[CH:7][C:2]([C:31]2[CH:32]=[CH:33][N:28]=[CH:29][CH:30]=2)=[CH:3][CH:4]=1)[C:9]([F:14])([F:15])[C:10]([F:13])([F:12])[F:11])#[N:44]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
To a solution of N2-[(1S)-1-(4-bromophenyl)-2,2,3,3,3-pentafluoropropyl]-N2-(cyanomethyl)-L-leucinamide (82 mg, 0.18 mmol), 4-pyridylboronic acid (30 mg, 0.24 mmol) and PdCl2(dppf) (14 mg, 0.02 mmol) in 2.5 mL DMF was added 2M Na2CO3 (0.25 mL). The mixture was heated to 95° C. for 2.5 h, then cooled and partitioned between aq. Na2CO3 and ether. The aqueous phase was washed with brine and dried over MgSO4. Purification by silica gel chromatography (65% to 95% ethyl acetate/hexanes gradient) provided the title compound.
Workup
- temperaturecooled
- custompartitioned between aq. Na2CO3 and ether
- washThe aqueous phase was washed with brine
- dry with materialdried over MgSO4
- customPurification by silica gel chromatography (65% to 95% ethyl acetate/hexanes gradient)
Sources & evidence
- ORD record
- ord-63eeb435ae0640d48afbb147e486a9cb
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07973037B2
Reaction notes
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