Sodium Carbonate → HCID 10288404, compound

HRID 2223518Notes

Reaction equation

HRID 2223518 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-8151806f504e41f08365db0f0d917815
Source dataset
uspto-grants-2008_05
Patent number
US07375134B2

Reaction notes

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