tert-Butyl carbamate → tert-butyl N-(3-fluoro-5-methyl-2-pyridinyl)carbamate

HRID 516

Reaction equation

HRID 516 reaction equation
CC(C)(C)OC(N)=O.Cc1cnc(Cl)c(F)c1>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.[Na+].[OH-].[Pd]>Cc1cnc(NC(=O)OC(C)(C)C)c(F)c1

Participants

7

Conditions

Temperature
100 °C

Procedure

diacetoxypalladium (15.42 mg, 0.07 mmol) and(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (39.8 mg, 0.07 mmol) were added to a degassed mixture of 2-chloro-3-fluoro-5-methylpyridine (100 mg, 0.69 mmol), tert-butyl carbamate (105 mg, 0.89 mmol) and 2-chloro-3-fluoro-5-methylpyridine (100 mg, 0.69 mmol) in dioxane (10 mL) at 21°C. The resulting mixture was stirred at 100 °C for 2 hours.Cooled. Adsorbed onto silica. The crude product was purified by flash silica chromatography, elution gradient 10 to 30% DCM in heptane. Pure fractions were evaporated to dryness to afford tert-butyl 3-fluoro-5-methylpyridin-2-ylcarbamate (40.0 mg, 25.7 %) as a cream solid. not pure enough to register ..

Sources & evidence

ORD record
ord-fde5e0f95519439ca9660af435fc14a6
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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