Potassium tert-butoxide → 5-Chloro-1H-pyrrolo[2,3-b]pyridine

HRID 877935

Reaction equation

CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([C:15]#[C:16][Si](C)(C)C)[C:11]([NH2:14])=[N:12][CH:13]=1>CN1CCCC1=O.[Cl-].[Na+].O>[Cl:7][C:8]1[CH:9]=[C:10]2[CH:15]=[CH:16][NH:14][C:11]2=[N:12][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of potassium tert-butoxide (36 g, 320 mmol) in N-methylpyrrolidone (70 ml) was heated to 80° C. under nitrogen. A solution of 5-chloro-3-(trimethyl-silanylethynyl)-pyridin-2-ylamine (2) (36 g, 160 mmol) in NMP (200 ml) was added dropwise via a dropping funnel. The reaction mixture was stirred at 80° C. for a further fifty minutes. The reaction mixture was allowed to cool to room temperature. Brine (500 ml) was added to the reaction mixture and extracted with diethyl ether (5×200 ml). The combined organics were washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography, using as eluent pentane/EtOAc 0% to 40%, and further recrystallised from cyclohexane to afford the title compound (10 g, 41%). 1H NMR (CDCl3) 6.5 (1H, s), 7.4 (1H, s), 8.0 (1H, s), 8.2 (1H, s), 10.4-10.6 (1H, brs). MS (ES+) 153.

Workup

temperatureto cool to room temperature
extractionextracted with diethyl ether (5×200 ml)
washThe combined organics were washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography
customfurther recrystallised from cyclohexane

Sources & evidence

ORD record: ord-2a62888913954fa18c61db75b334b7ad
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987454B2

Linked notes

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