Methanol → HCID 66731456, compound

HRID 1963184Notes

Reaction equation

HRID 1963184 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][N:17]=1)[C:11]([O:13][CH3:14])=[O:12].[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1B(O)O.CO>O.C(Cl)Cl.Cl[Pd]Cl>[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][N:17]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

8

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 2736842Methyl 2-chloropyridine-4-carboxylate

Product 1

HCID 66731456HCID 66731456, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (1.812 g, 13.11 mmol), methyl 2-chloroisonicotinate (3 g, 17.48 mmol), 2,4-dichlorophenylboronic acid (5.00 g, 26.23 mmol), PdCl2 (dppf) (0.380 g, 0.52 mmol), and MeOH (30.6 mL) were split in two 20 mL microwave vials and heated to 100° C. for 35 min in a single node microwave reactor. The reaction mixture was diluted with water and DCM, extracted with DCM and evaporated. Purified by automated flash chromatography using 5% EtOAc in heptane ->30% EtOAc over 15 CV at 280 nm. Methyl 2-(2,4-dichlorophenyl)isonicotinate (2.3 g, 47%) was isolated as a white solid. 1H NMR (400 MHz, cdcl3) δ 3.98 (s, 3H), 7.37 (dd, 1H), 7.53 (d, 1H), 7.57 (d, 1H), 7.86 (dd, 1H), 8.20 (s, 1H), 8.87 (d, 1H). MS m/z 282 (M+H)+

Workup

  1. extractionextracted with DCM
  2. customevaporated
  3. customPurified by automated flash chromatography

Sources & evidence

ORD record
ord-c4b5473c9b7f4adcaf3c0a51c2f2e4f0
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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