Diisopropylamine → HCID 67026987, compound

HRID 1404476Notes

Reaction equation

HRID 1404476 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]=[N:6][C:7]=1Cl.[CH:16]([B-](F)(F)F)=[CH2:17].[K+].[CH:23]1C=C(S([O-])(=O)=O)C=C(P(C2C=CC=C(S([O-])(=O)=O)C=2)C2C=CC=C(S([O-])(=O)=O)C=2)[CH:24]=1.[Na+].[Na+].[Na+].C(NC(C)C)(C)C.C(=O)(O)[O-].[Na+]>C(#N)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:23]([C:2]1[CH:3]=[C:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]=[N:6][C:7]=1[CH:16]=[CH2:17])=[CH2:24]

Participants

9

Reactant 5

HCID 7912DiisopropylamineHCID 516892Sodium BicarbonateHCID 6099338Trisodium 3,3',3''-phosphinetriyltris(benzene-1-sulphonate)HCID 23679353Potassium vinyltrifluoroborateHCID 86665190HCID 86665190, compound

Product 1

HCID 67026987HCID 67026987, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of tert-butyl 5-bromo-6-chloropyridine-3-carboxylate (24.0 g, 82.0 mmol) in acetonitrile (615 mL) and water (205 mL) were added potassium vinyltrifluoroborate (33.0 g, 246 mmol) and triphenylphosphine-3,3′,3″-trisulfonic acid trisodium salt (4.20 g, 7.38 mmol). Diisopropylamine (88.0 mL, 615 mmol) was added followed by palladium(II) acetate (0.553 g, 2.46 mmol). The mixture was heated to 75° C. After 16 h, the mixture was cooled to ambient temperature and saturated sodium bicarbonate was added. The mixture was washed with dichloromethane (3×) and the combined organics were washed with water, brine, and dried with magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→5% methanol/dichloromethane) gave the title compound. MS: m/z=232.3 (M+1).

Workup

  1. temperaturethe mixture was cooled to ambient temperature
  2. washThe mixture was washed with dichloromethane (3×)
  3. washthe combined organics were washed with water, brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (100% dichloromethane→5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-28442be37cf44642909b9015b4f4eafd
Source dataset
uspto-grants-2014_12
Patent number
US08912210B2

Reaction notes

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