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

HRID 2196671Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]([NH2:10])=[N:8][CH:9]=1)([O-:3])=[O:2].CC([O-])(C)C.[K+]>CN1C(=O)CCC1>[N+:1]([C:4]1[CH:5]=[C:6]2[CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:10][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 5-nitro-3-(phenylethynyl)pyridin-2-amine (356 mg, 1.0 eq.) in NMP (6 mL) was treated with KOt-Bu (2.2 eq.), and the solution was heated to 90° C. for 48 hours. The reaction mixture was purified directly by silica gel chromatography (eluting with a gradient of 100% hexanes to 40% EtOAc/hexanes) to afford 5-nitro-2-phenyl-1H-pyrrolo[2,3-b]pyridine (161 mg, 45%).

Workup

customThe reaction mixture was purified directly by silica gel chromatography (
washeluting with a gradient of 100% hexanes to 40% EtOAc/hexanes)

Sources & evidence

ORD record: ord-93c9ffa6f50b4bd6871a7c832dfd7ad7
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338452B2

Reaction notes

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