Methyl iodide → tert-butyl N-(2-chloro-3-methylfuro[2,3-c]pyridin-7-yl)-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate

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Reaction Steps

Di-tert-butyl (2-chlorofuro[2,3-c]pyridin-7-yl)imidodicarbonate (3.0 g, 8.15 mmol) in dry THF (100 mL) was cooled to −65° C. to −75° C. and LDA (1.8 M in THF/heptanes/ethylbenzene, 6.0 mL, 10.8 mmol), pre-cooled to the same temperature, was added slowly via syringe over a period of 10 min. The mixture was stirred for 1.5 h at −65° C. to −75° C. and then treated with methyl iodide (0.76 mL, 12.2 mmol) in dry THF added slowly via syringe. The mixture was allowed to warm to RT overnight and was quenched by the addition of water (50 mL) and diluted with EtOAc (100 mL). The phases were separated and the organic phase was dried over Na2SO4, and concentrated in vacuo leaving 3.2 g of a brown solid which was used without further purification. 1H NMR (400 MHz, CDCl3): δ 8.25 (d, J=5.5 Hz, 1H), 7.39 (d, J=5.5 Hz, 1H), 2.22 (s, 3H), 1.40 (s, 18H).

Provenance & Evidence