Hydrochloric Acid → 6-(3-Chloro-phenyl)-5-cyclopentyl-pyridine-2-carboxylic acid

HRID 632132Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:7](Br)[N:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.Cl>O.CN(C=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(Cl)Cl.[Pd](Cl)Cl>[Cl:23][C:24]1[CH:29]=[C:28]([C:7]2[N:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:10]=[CH:9][C:8]=2[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

6-Bromo-5-cyclopentyl-pyridine-2-carboxylic acid methyl ester (0.6 g, 2.1 mmol), bis(diphenylphosphino)ferrocene-palladium(II)dichloride methylene chloride complex (CAN 95464-05-4, 90 mg, 0.11 mmol) and potassium carbonate (0.37 g, 2.68 mmol) were added to a solution of 3-chlorophenylboronic acid (CAN 63503-60-6, 0.42 g, 2.69 mmol) in water (20 mL) and DMF (2 mL). The mixture was stirred for 48 h at 100° C. Its pH was adjusted to pH=3 with diluted hydrochloric acid. The mixture was extracted with methylene chloride (3×20 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure to give the title compound (130 mg, 20%) which was used in the next step without further purification; MS (EI): m/e=302.0 [M+H]+.

Workup

extractionThe mixture was extracted with methylene chloride (3×20 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-267f9319f02540528d61c72d5b4bb891
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321727B2

Reaction notes

Loading…