Ethyl Acetate → HCID 66720847, compound

HRID 1040365Notes

Reaction equation

HRID 1040365 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2[N:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][C:17]=2B2OC(C)(C)C(C)(C)O2)[CH:12]=[CH:13][C:14]=1[Cl:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:36]1[C:41]([Cl:42])=[CH:40][CH:39]=[CH:38][N:37]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>COCCOC.O.[Cl-].[Na+].O.C1C=CC([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)=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2[C:17]([C:36]3[C:41]([Cl:42])=[CH:40][CH:39]=[CH:38][N:37]=3)=[CH:18][CH:19]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[N:21]=2)[CH:12]=[CH:13][C:14]=1[Cl:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 169882,3-DichloropyridineHCID 66720732HCID 66720732, compound

Product 1

HCID 66720847HCID 66720847, compoundYield 28.8%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
85 °C

Procedure

Stir a solution of 850 mg (1.77 mmol) of methyl 6-[3-(benzyloxy)-4-chlorophenyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate and 524 mg (3.54 mmol) of 2,3-dichloropyridine in a mixture of 4 mL of DME and 2 mL of water for 15 minutes under argon, then add successively 734 mg (5.32 mmol) of K2CO3 and 61 mg (0.05 mmol) of Pd(PPh3)4 and heat the reaction mixture for 4 h at 85° C. Then distribute the reaction mixture between 10 mL of EtOAc and 10 mL of brine. Dry the organic phase over Na2SO4, filter, and then concentrate under reduced pressure. Purify the residue obtained on a silica column, eluting with a cyclohexane/EtOAc gradient from 0 to 20% of EtOAc. After concentration under reduced pressure, we obtain 237 mg of methyl 2′-[3-(benzyloxy)-4-chlorophenyl]-3-chloro-2,3′-bipyridine-6′-carboxylate in the form of oil.

Workup

  1. dry with materialDry the organic phase over Na2SO4
  2. filtrationfilter
  3. concentrationconcentrate under reduced pressure
  4. customPurify the residue
  5. customobtained on a silica column
  6. washeluting with a cyclohexane/EtOAc gradient from 0 to 20% of EtOAc
  7. concentrationAfter concentration under reduced pressure, we

Sources & evidence

ORD record
ord-86ca282996e840a0bd57503106b879a1
Source dataset
uspto-grants-2013_10
Patent number
US08552201B2

Reaction notes

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