Water → HCID 72792466, compound

HRID 1479895Notes

Reaction equation

HRID 1479895 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[N:7]=[C:6]([C:8]3[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=3)[CH:5]=[CH:4][CH:3]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 90040631Methyl 6'-chloro-2,2'-bipyridine-3-carboxylate

Product 1

HCID 72792466HCID 72792466, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

0.21 g (0.30 mmol) of (Ph3P)2PdCl2 is added under argan to a solution of 2.5 g (10.05 mmol) of methyl 6′-chloro-2,2′-bipyridine-3-carboxylate (1) in 70 ml of dioxane and the mixture is stirred for 30 min at room temperature. Thereafter, 1.98 g (12.08 mmol) of para-chlorophenylboronic acid, 4.17 g (30.17 mmol) of K2CO3 and 7 ml of H2O are added in succession to the mixture, and the mixture is stirred for 6 hours under reflux and subsequently left to stand overnight at RT. For work-up, the reaction mixture is poured into 100 ml of H2O and extracted repeatedly with CH2Cl2. The combined organic phases are dried over Na2SO4 and concentrated. The residue is purified by column chromatography over silica gel using heptane/ethyl acetate (7:3) as the mobile phase. This gives 2.7 g (82.7%) of product as a solid. M.p.: 120.5° C.; 1H NMR (CDCl3) δ 8.75 (dd, 1H), 8.17 (dd, 1H), 8.00 (m, 2H, C6H4Cl), 7.95 (dd, 1H), 7.92 (dd, 1H), 7.28 (dd, 1H), 7.45 (m, 2H, C6H4Cl), 7.40 (dd, 1H), 3.60 (s, 3H, COOMe).

Workup

  1. stirringthe mixture is stirred for 6 hours
  2. temperatureunder reflux
  3. waitsubsequently left
  4. waitto stand overnight at RT
  5. extractionextracted repeatedly with CH2Cl2
  6. dry with materialThe combined organic phases are dried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue is purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-ac1227bc54af4c4882cf58c6a09ae0bb
Source dataset
uspto-grants-2016_08
Patent number
US09409881B2

Reaction notes

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