Ethanol → 1H-Pyrrolo[2,3-b]pyridine-3-carbonitrile, 5-(2-thienyl)-

HRID 1432328Notes

Reaction equation

C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[C:13]3[C:12]([C:24]#[N:25])=[CH:11]2)(=O)=O)C=CC=CC=1.CCO.[OH-].[Na+]>ClCCl.CO>[S:20]1[CH:21]=[CH:22][CH:23]=[C:19]1[C:17]1[CH:18]=[C:13]2[C:12]([C:24]#[N:25])=[CH:11][NH:10][C:14]2=[N:15][CH:16]=1

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of 11 (18.3 mg, 50.1 μmol), EtOH (2.0 mL) and 10% aqueous NaOH (1.0 mL) was refluxed (oil bath temp. 105° C.) for 40 min. The mixture was poured onto water (3 mL), extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried (MgSO4) and concentrated. The product was isolated by PTLC using dichloromethane:methanol (19:1) as eluent to give 12 as a white solid (7.6 mg, 68%); 1H NMR (400 MHz, CDCl3) δ 10.30-10.10 (bs, NH), 10.74 (d, J=1.9 Hz, 1H), 8.31 (d, J=1.9 Hz, 1H), 7.90 (s, 1H), 7.39 (m, 2H), 7.16 (dd, J=5.0, 3.6 Hz, 1H).

Workup

additionThe mixture was poured onto water (3 mL)
extractionextracted with ethyl acetate (3×10 mL)
dry with materialThe combined organic extracts were dried (MgSO4)
concentrationconcentrated
customThe product was isolated by PTLC

Sources & evidence

ORD record: ord-87a246b9af0f445694427eae00478655
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612086B2

Reaction notes

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