Methyl chloroformate → HCID 59598311, compound

HRID 2266035Notes

Reaction equation

[CH2:1]([NH:5][C:6]1[C:11]([CH:12]=[C:13](Br)Br)=[CH:10][CH:9]=[C:8]([C:16]([F:19])([F:18])[F:17])[N:7]=1)[CH2:2][CH2:3][CH3:4].[Li]CCCC.CCCCCC.Cl[C:32]([O:34][CH3:35])=[O:33]>C1COCC1.C([O-])(O)=O.[Na+].[NH4+].[Cl-]>[CH3:35][O:34][C:32](=[O:33])[C:13]#[C:12][C:11]1[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[N:7][C:8]([C:16]([F:19])([F:18])[F:17])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of butyl-[3-(2,2-dibromo-vinyl)-6-trifluoromethyl-pyridin-2-yl]-amine (1.02 g, 2.54 mmol) in THF under nitrogen at −78° C. was slowly treated with 2.5 M BuLi in hexane (2.0 mL, 5.00 mmol) and then stirred for 30 min at −78° C. and 30 min at −0° C. The mixture was treated with methyl chloroformate (0.235 mL, 3.05 mmol) at −78° C. and warmed to 0° C. for 1 hr. The mixture was diluted with 1:1 mixture of saturated NaHCO3 and NH4Cl solution and the aqueous layer was extracted with ether (×3). The combined organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by chromatography (Hex/EtOAc=10/1) to give the title compound (78 mg, 10%).

Workup

temperaturewarmed to 0° C. for 1 hr
extractionthe aqueous layer was extracted with ether (×3)
dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude residue was purified by chromatography (Hex/EtOAc=10/1)

Sources & evidence

ORD record: ord-b13a57384d86436caee64e75374c70e2
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858621B2

Reaction notes

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