3-Chlorophenol → 6-Bromo-4-(3-chlorophenoxy)-1,2,3,4-tetrahydro-[1,8]naphthyridine

HRID 1819110Notes

Reaction equation

HRID 1819110 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH:5]2[OH:12].[Cl:13][C:14]1[CH:15]=[C:16](O)[CH:17]=[CH:18][CH:19]=1>CO.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH:5]2[O:12][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:13])[CH:19]=1

Participants

4

Reactant 2

HCID 79333-ChlorophenolHCID 578858646-Bromo-1,2,3,4-tetrahydro-[1,8]naphthyridin-4-ol

Product 1

HCID 578858956-Bromo-4-(3-chlorophenoxy)-1,2,3,4-tetrahydro-[1,8]naphthyridineYield 60%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

6-Bromo-1,2,3,4-tetrahydro-[1,8]naphthyridin-4-ol (225 mg) was reacted with 3-chlorophenol (0.30 mL) as in General Procedure 12. Basic alumina chromatography using a gradient of 0-1% methanol/methylene chloride as the eluting solvent gave the title compound as a white film (60% yield). LCMS: m/z=339 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 2.00 (m, 1H), 2.21 (m, 1H), 3.40 (m, 1H), 3.51 (m, 1H), 5.04 (s, 1H), 5.27 (t, J=3.9 Hz, 1H), 6.87 (d, J=8.3 Hz, 1H), 7.00 (m, 2H), 7.24 (m, 1H), 7.48 (d, J=2.1 Hz, 1H), 8.06 (d, J=2.1 Hz, 1H).

Sources & evidence

ORD record
ord-311cd01f0e074751b3d492ab91b1620e
Source dataset
uspto-grants-2009_10
Patent number
US07601716B2

Reaction notes

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