Water → HCID 22462076, compound

HRID 1936543Notes

Reaction equation

[CH:1]([OH:4])([CH3:3])[CH3:2].N12CCCC1=NCCC2.[Cl:14][C:15]1[CH:23]=[C:22]([F:24])[C:21]([C:25]2[C:29]([Br:30])=[C:28]([C:31]([F:34])([F:33])[F:32])[N:27]([CH3:35])[C:26]=2[Br:36])=[CH:20][C:16]=1[C:17](O)=[O:18].O>CN(C=O)C>[Cl:14][C:15]1[CH:23]=[C:22]([F:24])[C:21]([C:25]2[C:29]([Br:30])=[C:28]([C:31]([F:33])([F:34])[F:32])[N:27]([CH3:35])[C:26]=2[Br:36])=[CH:20][C:16]=1[C:17]([O:4][CH:1]([CH3:3])[CH3:2])=[O:18]

Participants

Conditions

Temperature: 40 °C

Procedure

Isopropanol (0.2 g; 3.2 mmoles), 1,5-diazabicyclo -[4.3.0]non-5-ene (0.21 g; 1.6 mmoles) are added to a mixture of 2-chloro-5-(2,4-dibromo-1-methyl-5-trifluorometh-ylpyrrol-3-yl)-4-fluorobenzoic acid (0.8 g; 1.6 mmoles) and N,N′-carbonyldiimidazole (0.77 g; 1.6 mmoles) in DMF (4 ml) heated to 40° C. for 1.5 hours, and the mixture is heated to 40° C. for 2 hours. The reaction mixture is poured into water (10 ml), extracted with ethyl ether (3×20 ml), the ether phase is washed with a saturated solution of sodium chloride, anhydrified on sodium sulfate and concentrated in a rotavapor. The raw product obtained (0.8 g) is chromatographed on silica gel, eluating with n-hexane/ethyl acetate 90:10. 0.4 g of product are obtained in the form of a colourless oil.

Workup

temperaturethe mixture is heated to 40° C. for 2 hours
extractionextracted with ethyl ether (3×20 ml)
washthe ether phase is washed with a saturated solution of sodium chloride
concentrationconcentrated in a rotavapor
customThe raw product obtained (0.8 g)
customis chromatographed on silica gel

Sources & evidence

ORD record: ord-1181b1eb59554d0189ab71da8ffd3cb8
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06391827B1

Reaction notes

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