Potassium Carbonate → HCID 66818371, compound

HRID 1024693Notes

Reaction equation

[CH:1]([O:4][C:5](=[O:17])[C:6]1[CH:11]=[C:10]([O:12][CH:13]([CH3:15])[CH3:14])[N:9]=[C:8]([OH:16])[CH:7]=1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].F[C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=1.OC1N=CC=CC=1C([O-])=O>CN(C=O)C>[CH:1]([O:4][C:5](=[O:17])[C:6]1[CH:11]=[C:10]([O:12][CH:13]([CH3:15])[CH3:14])[N:9]=[C:8]([O:16][C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=2)[CH:7]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

2-Hydroxy-6-isopropoxy-isonicotinic acid isopropyl ester (0.5 g, 2.09 mmol) and 0.577 g (4.18 mmol) potassium carbonate was dissolved in 5 ml of dry DMF. 0.25 g (2.09 mmol) of 4-fluorobenzonitrile, dissolved in 5 ml of DMF, was added to the stirred solution of hydroxynicotinate over a period of 15 min and then the contents of the reaction flask were stirred overnight at 100° C. Reaction mixture was concentrated and the residue was dissolved in 100 ml of ethylacetate and washed with water. Ethyl acetate layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 0.3 g of required product which was used for the next step without further purification. 1H NMR (CDCl3): δ 1.2 (6H, d), 1.35 (6H, d), 4.8 (1H, m), 5.25 (1H, m), 7.2 (3H, m), 7.7 (3H, m).

Workup

customReaction mixture
concentrationwas concentrated
dissolutionthe residue was dissolved in 100 ml of ethylacetate
washwashed with water
dry with materialEthyl acetate layer was dried over anhydrous sodium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-39c9114ead0f4896826e1f7dde9b6ca8
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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