Sodium Carbonate → HCID 10288404, compound

HRID 1620914Notes

Reaction equation

HRID 1620914 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:16][C@H:17]([C:22]([NH:24][CH2:25][C:26]#[N:27])=[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([O-])([O-])=O.[Na+].[Na+]>CN(C=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:26]([CH2:25][NH:24][C:22](=[O:23])[C@H:17]([CH2:18][CH:19]([CH3:21])[CH3:20])[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:15])([F:14])[C:10]([F:13])([F:12])[F:11])#[N:27]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 10195230HCID 10195230, compound

Product 1

HCID 10288404HCID 10288404, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of N2-[(1S)-1-(4-bromophenyl)-2,2,3,3,3-pentafluoropropyl]-N1-(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

  1. temperaturecooled
  2. custompartitioned between aq. Na2CO3 and ether
  3. washThe aqueous phase was washed with brine
  4. dry with materialdried over MgSO4
  5. customPurification by silica gel chromatography (65% to 95% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-fc44d149f4104145916ff9d192155213
Source dataset
uspto-grants-2014_07
Patent number
US08772336B2

Reaction notes

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