Sodium hydride → HCID 57537477, compound

HRID 1693694Notes

Reaction equation

[Br:1][C:2]1[C:3]([Cl:12])=[C:4]2[C:10]([I:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:15][Si:16]([CH3:23])([CH3:22])[CH2:17][CH2:18][O:19][CH2:20]Cl>CN(C=O)C>[Br:1][C:2]1[C:3]([Cl:12])=[C:4]2[C:10]([I:11])=[CH:9][N:8]([CH2:20][O:19][CH2:18][CH2:17][Si:16]([CH3:23])([CH3:22])[CH3:15])[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5-Bromo-4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (7.68 g, 21.5 mmol) was dissolved in 100 mL dry DMF and cooled to 0° C. Sodium hydride (60% suspension in mineral oil, 1.03 g, 25.8 mmol) was added cautiously over 5 min. The mixture was cooled to −42° C. and 2-trimethylsilanyl-ethoxymethylchloride (5 mL, 28 mmol) was added slowly over 10 min. The mixture was stirred at −42° C. for 2 h and quenched with 200 mL saturated ammonium chloride solution and 200 mL water. The aqueous mixture was extracted with dichloromethane and the organic phase was washed with water, dried and concentrated to afford 5-Bromo-4-chloro-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (10.1 g, 20.7 mmol, 96% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.53 (s, 1H), 8.07 (s, 1H), 5.57 (s, 2H), 3.49 (t, J=8 Hz, 2H), 0.79 (t, J=8 Hz, 2H), −0.11 (s, 9H). MS: m/z 486.7/488.7 (M+H+).

Workup

temperatureThe mixture was cooled to −42° C.
customquenched with 200 mL saturated ammonium chloride solution and 200 mL water
extractionThe aqueous mixture was extracted with dichloromethane
washthe organic phase was washed with water
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-f26f2d276a9d46e3b60a5af6e3546e4c
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158647B2

Reaction notes

Loading…