Sodium Carbonate → HCID 9840916, compound

HRID 2305095Notes

Reaction equation

HRID 2305095 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([O:14][CH2:15][C@@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3[CH3:21])[CH:10]=[N:11][C:12]=2Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(B(O)O)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1.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.O>[C:1]1([C:7]2[CH:8]=[C:9]([O:14][CH2:15][C@@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3[CH3:21])[CH:10]=[N:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 54177843HCID 54177843, compound

Product 1

HCID 9840916HCID 9840916, compoundYield 76.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a solution of 5-phenyl-6-chloro-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine (110 mg, 0.36 mmol) in benzene (2.0 mL) were added sodium carbonate (2.0 M, 1.0 mL), tetrakis(triphenylphosphine)palladium(0) (15 mg, 0.013 mmol) and phenylboronic acid (53 mg, 0.43 mmol). The reaction mixture was refluxed overnight, and then cooled to room temperature. Water (2 mL) was added, and solid sodium bicarbonate was added until the aqueous layer was saturated. The mixture was extracted with EtOAc, which was dried over MgSO4, filtered and concentrated. The residue was chromatographed on a silica gel column, eluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90 to afford a light yellowish oil (74 mg, 67%). MS (CI/NH3) m/z 303 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 1.65-2.10 (m, 4H), 2.27-2.38 (m, 1H), 2.49 (s, 3H), 2.63-2.72 (m, 1H), 3.08-3.16 (m, 1H), 3.93-4.05 (m, 2H), 7.24 (d, J=3.0 HZ, 1H), 7.44-7.48 (m, 5H), 8.09 (d, J=3.0 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. extractionThe mixture was extracted with EtOAc, which
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a silica gel column
  7. washeluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90

Sources & evidence

ORD record
ord-4e0b7a00954c43c597e01823551c215c
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

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