Iodoethane → HCID 69482004, compound

HRID 2364352Notes

Reaction equation

HRID 2364352 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:25])=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.I[CH2:27][CH3:28]>O1CCCC1>[CH2:27]([N:16]1[C:17]2[C:12](=[N:11][CH:10]=[C:9]([CH2:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:18]=2)[C:13]([OH:25])=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]1=[O:19])[CH3:28]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69482004HCID 69482004, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to that described in example 316 step 1, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (160 mg, 0.468 mmol), lithium (bis-trimethylsilyl)amide (0.94 mL of a 1 M solution in tetrahydrofuran, 0.940 mmol), and iodoethane (0.22 mL, 2.81 mmol) was prepared ethyl 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (170 mg, 95% yield) as a yellow oil. The product was carried on without further purification. 1H NMR (CDCl3) δ 8.37 (s, 1 H), 7.34 (s, 1 H), 7.10-7.05 (m, 2 H), 6.95-6.91 (m, 2 H), 4.39 (m, 2 H), 4.11 (m, 2 H), 4.06 (s, 2 H), 1.35 (m, 3 H), 1.15 (m, 3 H); MS m/z 393 (M+23).

Sources & evidence

ORD record
ord-e4f4a9341f8d4d97aebcebcdb14a1338
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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