Potassium Carbonate → 3-cyclopentyl-2-[4-(3-fluoro-pyridin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester

HRID 2381377Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:19])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14](I)[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[F:20][C:21]1[C:22]([OH:27])=[N:23][CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:19])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([O:27][C:22]2[C:21]([F:20])=[CH:26][CH:25]=[CH:24][N:23]=2)[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 3-cyclopentyl-2-(4-iodo-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester (0.38 g, 1 mmol) in N,N-dimethylformamide (10 mL) was treated with 3-fluoro-pyridin-2-ol (0.15 g, 1 mmol) and potassium carbonate (0.16 g, 1.2 mmol). The reaction was heated at 120° C. for 4 h and then concentrated in vacuo. The residue was partitioned between water and methylene chloride. The aqueous layer was back extracted with methylene chloride. The combined organics were washed with a saturated aqueous sodium chloride solution, and then concentrated in vacuo. Chromatography (1/1 ethyl acetate/petroleum ether) afforded 3-cyclopentyl-2-[4-(3-fluoro-pyridin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester (0.19 g, 53%).

Workup

concentrationconcentrated in vacuo
customThe residue was partitioned between water and methylene chloride
extractionThe aqueous layer was back extracted with methylene chloride
washThe combined organics were washed with a saturated aqueous sodium chloride solution
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c1e758e022f840d9bf17e085e8f31fb9
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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