Tetrahydrofuran → HCID 58551097, compound

HRID 1908097Notes

Reaction equation

[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][NH:3]1.C([O-])([O-])=O.[K+].[K+].C1[CH2:22][O:21][CH2:20][CH2:19]1.Br[CH2:24][CH2:25][O:26][CH3:27]>CN(C=O)C>[CH3:22][O:21][CH2:20][CH2:19][N:3]1[CH:4]=[CH:5][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:7][C:2]1=[O:1].[CH3:27][O:26][CH2:25][CH2:24][O:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][N:3]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 2-oxo-1H-pyridine-4-carboxylate (2.00 g, 13.1 mmol), K2CO3 (3.61 g, 26.1 mmol), THF (48 mL), DMF (38 mL) and 1-bromo-2-methoxy-ethane (3.63 g, 2.45 mL, 26.1 mmol) were combined and the mixture was stirred at 80° C. for 2 d. The reaction was filtered using ethyl acetate and the solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel (0-100% ethyl acetate in hexane) to yield methyl 1-(2-methoxyethyl)-2-oxo-1,2-dihydropyridine-4-carboxylate [(1.22 g, 44%), ESI-MS m/z calc. 211.1. found 212.3 (M+1)+; Retention time: 0.57 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 8.35 (d, J=5.2 Hz, 1H), 7.41 (d, J=5.2 Hz, 1H), 7.21 (s, 1H), 4.47-4.36 (m, 2H), 3.89 (s, 3H), 3.71-3.64 (m, 2H), 3.30 (s, 3H)] and methyl 2-(2-methoxyethoxy)isonicotinate [(405 mg), ESI-MS m/z calc. 211.1. found 212.1 (M+1)+; Retention time: 1.04 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 7.75 (d, J=7.0 Hz, 1H), 6.86 (s, 1H), 6.55 (d, J=7.0 Hz, 1H), 4.09 (t, J=5.2 Hz, 2H), 3.85 (s, 3H), 3.58 (t, J=5.2 Hz, 2H), 3.23 (s, 3H)].

Workup

filtrationThe reaction was filtered
customthe solvent was evaporated under reduced pressure
customthe residue was purified by column chromatography on silica gel (0-100% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-4ef1af3d858544ca8ae76a6dc85f0618
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598164B2

Reaction notes

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