Ammonium Chloride → HCID 53909268, compound

HRID 1378376Notes

Reaction equation

C([Li])CCC.Br[C:7]1[N:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][CH:8]=1.[C:15]([N:19]=[C:20]=[O:21])([CH3:18])([CH3:17])[CH3:16].[NH4+].[Cl-]>C1COCC1>[C:15]([NH:19][C:20]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([O:13][CH3:14])[N:12]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyllithium (18.25 mmole) was added dropwise to a cooled solution of 6-bromo-2-methoxypyridine (3.12 g, 16.6 mmole, prepared from 2,6-dibromopyridine (Aldrich) according to Comins and Killpack, J. Org. Chem., 55:69-73 (1990)) in 40 mL of THF at -78° C., the resulting orange solution was stirred for 20 minutes at -78° C., and t-butylisocyanate (26.3 mmole) was added with a syringe. The mixture was stirred for 30 minutes at -78° C., warmed to room temperature, then saturated NH4Cl (20 mL) was added. The layers were separated, and the aqueous layer was extracted with methylene chloride (2×20 mL). The combined organic layers were dried over MgSO4 and concentrated, and the residue was chromatographed on silica gel, eluting with 10% to 25% ethyl acetate in hexane, to provide 2.93 g of the title compound as an oil. MS: 209 (M+H)+ ; 1H NMR (CDCl3) δ: 7.85-7.68 (m, 3H), 6.87 (d, J=8 Hz, 1H), 3.96 (s, 3H), 1.49 (s, 9H).

Workup

stirringThe mixture was stirred for 30 minutes at -78° C.
temperaturewarmed to room temperature
customThe layers were separated
extractionthe aqueous layer was extracted with methylene chloride (2×20 mL)
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated
customthe residue was chromatographed on silica gel
washeluting with 10% to 25% ethyl acetate in hexane

Sources & evidence

ORD record: ord-73f752adcc5a4a6eb1dec61c2651b48c
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05668141

Reaction notes

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