Potassium Carbonate → HCID 10323257, compound

HRID 1180374Notes

Reaction equation

HRID 1180374 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:34])[C@@H:6]([O:11][C@H:12]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:13]1[CH:18]=[CH:17][C:16](B2OC(C)(C)C(C)(C)O2)=[CH:15][CH:14]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2].Br[C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=2)=[CH:38][CH:37]=1.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[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:1]([CH2:3][NH:4][C:5](=[O:34])[C@@H:6]([O:11][C@H:12]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:13]1[CH:14]=[CH:15][C:16]([C:36]2[CH:41]=[CH:40][C:39]([C:42]3[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=3)=[CH:38][CH:37]=2)=[CH:17][CH:18]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 6162834-(4-Bromophenyl)pyridineHCID 86605378HCID 86605378, compound

Product 1

HCID 10323257HCID 10323257, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

(2S)-N-(cyanomethyl)-4-methyl-2-({(R)-phenyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}oxy)pentanamide (100 mg, 0.216 mmol), 4-(4-bromophenyl)pyridine (56 mg, 0.238 mmol) and 2M K2CO3 (324 ul, 0.648 mmol) were dissolved in 1.6 ml DMF and the solution was degassed 3 times. PdCl2(dppf) (4.8 mg, 0.03 mmol) was added and the mixture was stirred overnight at 80° C. The solution was cooled, poured into 8 ml NaHCO3 (sat.) and extracted 3 times with 2 ml ethyl acetate. The combined organic layers were then washed with 4× water, then dried with Na2SO4. (2S)-N-(cyanomethyl)-4-methyl-2-{[(R)-phenyl(4′-pyridin-4-yl-1,1′-biphenyl-4-yl)methyl]oxy}pentanamide was obtained after purification on silica gel (2% MeOH/38% ethyl acetate/60% hexanes).

Workup

  1. customthe solution was degassed 3 times
  2. temperatureThe solution was cooled
  3. extractionextracted 3 times with 2 ml ethyl acetate
  4. washThe combined organic layers were then washed with 4× water
  5. dry with materialdried with Na2SO4

Sources & evidence

ORD record
ord-28163afe9d2748afba324715c13738ab
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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