Binap, (A+-)- → 1-Methyl-6-(2-oxa-6-azaspiro[3,3]heptan-6-yl)-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile

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Reaction Conditions

Reaction Steps

6-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine 5-carbonitrile (300 mg, 1.27 mmol), sodium tert-butoxide (366 mg, 3.81 mmol), racemic BINAP (79 mg, 0.127 mmol), Pd2 dba3 (58 mg, 0.064 mmol), and 2-oxo-6-azaspiro[3,3]heptane, 0.5 oxylic acid salt (274 mg, 1.91 mmol) were combined in DMA (12 mL) under N2. The reaction mixture was heated at 102° C. in a microwave for 1 hour and was then diluted with DCM, washed with brine, dried over MgSO4, and concentrated. Purification by silica gel chromatography (2-5% MeOH in DCM) gave the title compound as a pale yellow solid (222 mg, 69%). 1H NMR (500 MHz, CDCl3) δ ppm 7.21 (d, 1H, J=3.5 Hz), 6.60 (s, 1H), 6.58 (d, 1H, J=3.5 Hz), 4.89 (s, 4H), 4.34 (s, 4H), 3.73 (s, 3H). ESI-MS m/z [M+H]+ calc'd for C14H14F4O, 255; found 255.

Provenance & Evidence