Hydrochloric Acid → HCID 68008364, compound

HRID 533161Notes

Reaction equation

HRID 533161 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5](Cl)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:13]([Sn](CCCC)(CCCC)C=C)[CH2:14]CC.Cl.C(=O)(O)[O-].[Na+].[C:34]1(C)C=CC=C[CH:35]=1>C1(P([Pd](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:13]([C:5]1[N:4]=[CH:3][C:2]([CH:34]=[CH2:35])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])=[CH2:14]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 81998TributylvinyltinHCID 516892Sodium BicarbonateHCID 2763343Methyl 5-bromo-2-chloronicotinate

Product 1

HCID 68008364HCID 68008364, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 178420554HCID 178420554, compoundCatalyst

Conditions

Temperature
110 °C

Procedure

Methyl 5-bromo-2-chloronicotinate (6.9 g, 27.6 mmol) was dissolved into toluene (100 mL). Tributyl(vinyl)tin (19.7 g, 62.1 mmol) was added, followed by tetrakistriphenylphosphinopalladium (2.5 g, 2.1 mmol), and the reaction heated at 110° C. for 3 h. The reaction mixture was poured onto 2 N HCl (100 mL) and stirred for 30 min, then neutralized with saturated sodium bicarbonate. The organic layer was removed, concentrated and purified over silica gel using automated chromatography to give 4.5 g (86%) of the compound. LC-MS (M+H)=190.1.

Workup

  1. customThe organic layer was removed
  2. concentrationconcentrated
  3. custompurified over silica gel using automated chromatography

Sources & evidence

ORD record
ord-f821f7e0e89d4d5bbf7211364d9b9990
Source dataset
uspto-grants-2014_10
Patent number
US08853237B2

Reaction notes

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