Pyridine → 3-Bromo-1-(tert-butyl-dimethyl-silanyl)-5-pyridin-3-yl-1h-pyrrolo[2,3-b]pyridine

HRID 1886818Notes

Reaction equation

[Br:1]Br.[C:3]([Si:7]([CH3:24])([CH3:23])[N:8]1[C:12]2=[N:13][CH:14]=[C:15]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:16]=[C:11]2[CH:10]=[CH:9]1)([CH3:6])([CH3:5])[CH3:4].N1C=CC=CC=1.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[Br:1][C:10]1[C:11]2[C:12](=[N:13][CH:14]=[C:15]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:16]=2)[N:8]([Si:7]([C:3]([CH3:6])([CH3:5])[CH3:4])([CH3:24])[CH3:23])[CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of bromine (0.166 mL, 0.0032 mol) in 1 mL of CCl4 was added dropwise to a stirred solution of 20 (1.0 g, 0.0032 mol) and pyridine (0.314 mL, 0.0039 mol) in dry CHCl3 (30 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 h and then neutralized with 10 mL of a mixture of sodium bicarbonate-sodium thiosulfate (1:1). The organic layer was separated and further extracted with dichloromethane (3×10 mL) and the combined organics dried and concentrated in vacuo. The residue was subjected to flash chromatography (30% EtOAc-70% hexanes) to give 0.97 g (78%) of the desired material 21. 1H NMR CDCl3 8.9 (s, 1H), 8.55 (d, 1H), 8.4 (d, 1H), 8.0 (d, 1H), 7.9 (d, 1H), 7.4 (dd, 1H), 7.2 (s, 1H), 0.9 (s, 9H), 0.5 (s, 6H).

Workup

customThe organic layer was separated
extractionfurther extracted with dichloromethane (3×10 mL)
customthe combined organics dried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d2153a386fae470e97a263baac10518f
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501446B2

Reaction notes

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