Sodium Carbonate → HCID 59543444, compound

HRID 1798939Notes

Reaction equation

HRID 1798939 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][C:22]1[CH:27]=[C:26](B(O)O)[CH:25]=[CH:24][N:23]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([C:26]3[CH:25]=[CH:24][N:23]=[C:22]([CH3:21])[CH:27]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 41926642-Methylpyridine-4-boronic acidHCID 21931358tert-butyl 4-(5-bromopyridin-2-yl)piperidine-1-carboxylate

Product 1

HCID 59543444HCID 59543444, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolvent2×

Procedure

5-Bromo-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (0.6 g, 1.76 mmol), 2-methylpyridine-4-boronic acid (264 mg, 1.9 mmol), bis(triphenylphosphine)-palladium(II)chloride (0.06 g, 0.09 mmol), 1 M Na2CO3 (4 ml) and acetonitrile (4 ml) were mixed in a 5 ml microwave vial. Another (2 ml) and acetonitrile (2 ml) were added. The reaction mixture was heated for 1500 sec. at 85° C. Water layer was removed. The acetonitrile phase was added DCM (20 mL). The organic phase was filtered and evaporated in vacuo. The crude mixture was purified on a silicagel column with EtOAc/heptane (4:1) and then EtOAc/heptane (9:1). The product was collected as a clear oil (540 mg, 87%).

Workup

  1. temperatureThe reaction mixture was heated for 1500 sec
  2. customat 85° C
  3. customWater layer was removed
  4. additionThe acetonitrile phase was added DCM (20 mL)
  5. filtrationThe organic phase was filtered
  6. customevaporated in vacuo
  7. customThe crude mixture was purified on a silicagel column with EtOAc/heptane (4:1)
  8. customThe product was collected as a clear oil (540 mg, 87%)

Sources & evidence

ORD record
ord-987c5c1c274548beb7172db173de4e73
Source dataset
uspto-grants-2013_01
Patent number
US08344001B2

Reaction notes

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