Potassium tert-butoxide → 5-chloro-2-(1-methylcyclopropyl)-1H-pyrrolo[2,3-c]pyridine

HRID 513081Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:9]#[C:10][C:11]2([CH3:14])[CH2:13][CH2:12]2)[CH:3]=1.CC([O-])(C)C.[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:9]=[C:10]([C:11]3([CH3:14])[CH2:13][CH2:12]3)[NH:8][C:5]2=[CH:6][N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-chloro-4-((1-methylcyclopropyl)ethynyl)pyridin-3-amine (3.0 g, 15 mmol) in DMF (50 mL) was added t-BuOK (3.3 g, 29 mmol) under N2 atmosphere. The mixture was heated at 80° C. overnight and quenched with H2O (100 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (50 mL×3). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and purified by chromatography on silica gel (3% EtOAc in petroleum ether) to afford 5-chloro-2-(1-methylcyclopropyl)-1H-pyrrolo[2,3-c]pyridine (2.2 g, 73%). 1H-NMR (CDCl3, 300 MHz) δ 9.79 (br s, 1H), 8.37 (s, 1H), 7.36 (s, 1H), 6.16 (s, 1H), 1.51 (s, 3H), 1.09 (m, 2H), 0.89 (m, 2H).

Workup

customquenched with H2O (100 mL)
customThe organic layer was separated
extractionthe aqueous layer was extracted with ethyl acetate (50 mL×3)
washThe combined organic layer was washed with brine
dry with materialdried over anhydrous Na2SO4
custompurified by chromatography on silica gel (3% EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-66dadb659eb34e6aab09b82a7fa90051
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102672B2

Reaction notes

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