Potassium Carbonate → HCID 58946494, compound

HRID 1038109Notes

Reaction equation

HRID 1038109 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11](B2OC(C)(C)C(C)(C)O2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:23][C:24]1[CH:29]=[CH:28][C:27](I)=[CH:26][C:25]=1[F:31].C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>[Pd+2].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].ClCCl.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:27]2[CH:28]=[CH:29][C:24]([Br:23])=[C:25]([F:31])[CH:26]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27250061-Bromo-2-fluoro-4-iodobenzeneHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 58946494HCID 58946494, compound

Reagents, catalysts & solvents 2

HCID 178478475HCID 178478475, compoundCatalystHCID 962WaterSolvent

Procedure

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (14AB) (4.0 g, 12.9 mmol, 1 equiv), 1-Bromo-2-fluoro-4-iodo-benzene (15AB) (5.84 g, 19.4 mmol, 1.5 equiv), potassium carbonate (5.4 g, 38.8 mmol, 3 equiv), and a (4v:1v) mixture of 1,4-dioxane and water (120 mL: 30 mL) were all added in a pressure vessel (350 mL) and the mixture was bubbled with nitrogen gas for about 10 minutes. To this mixture was added dichloro[1,1′-bis(diphenylphosphino)ferrocene] palladium (II)/dichloromethane adduct (1.05 g, 1.29 mmol, 0.1 equiv), and the reaction vessel was tightly capped, placed in an oil bath at 80° C., and stirred overnight.

Workup

  1. additionall added in a pressure vessel (350 mL)
  2. customthe mixture was bubbled with nitrogen gas for about 10 minutes
  3. customthe reaction vessel was tightly capped
  4. customplaced in an oil bath at 80° C.

Sources & evidence

ORD record
ord-e7c01d123b40484eb8f5600f243c16e6
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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