Sodium hydride → HCID 59238656, compound

Participants

Reaction Steps

To a stirred solution of azaindole (XXVa-101) (12.65 g, 42.5 mmol) in DMF (120 mL) was added 60% NaH dispersion in mineral oil (2.04 g, 51.0 mmol) portionwise over 3 min. After 15 min, tert-butyldimethylchlorosilane (8.33 g, 55.3 mmol) was added and the mixture stirred for a further 66 h. The mixture was diluted with EtOAc (150 mL) and saturated NaHCO3 solution (100 mL) and partitioned. The aqueous layer was extracted with EtOAc (4×150 mL) and CH2Cl2 (100 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated to yield a honey coloured viscous oil. This was purified by means of SGC using hexane:CH2Cl2 (gradient elution from 100:0 to 0:100, v/v) followed by CH2Cl2:MeOH (gradient elution from 100:0 to 90:10, v/v) to afford the silylated azaindole (XXVIIa-101) (15.37 g, 87%). 1H NMR (400 MHz, CDCl3) δ 0.62 (s, 6H), 0.92 (s, 9H), 1.68 (m, 1H), 1.87-1.93 (m, 2H), 2.05-2.10 (m, 1H), 2.18-2.26 (m, 1H), 2.36-2.43 (m, 1H), 2.57-2.63 (m, 2H), 2.83-2.86 (m, 5H), 3.75 (t, J=4.7 Hz, 2H), 3.82 (t, J=6.0 Hz, 2H), 6.02-6.05 (m, 1H), 6.49 (d, J=3.5 Hz, 1H), 7.21 (d, J=3.5 Hz, 1H), 7.81 (d, J=2.3 Hz, 1H), 8.33 (d, J=2.3 Hz, 1H).

Provenance & Evidence