Benzyl Bromide → HCID 10126425, compound

HRID 916925Notes

Reaction equation

[CH2:1](Br)[C:2]1C=CC=C[CH:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:21][C:20](=[O:22])[C:19]([C:23]([O:25][CH3:26])=[O:24])=[CH:18][C:17]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:12][CH:11]=1>>[CH2:3]([O:22][C:20]1[C:19]([C:23]([O:25][CH3:26])=[O:24])=[CH:18][C:17]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[C:16]([C:13]2[CH:12]=[CH:11][C:10]([Cl:9])=[CH:15][CH:14]=2)[N:21]=1)[CH:2]=[CH2:1]

Participants

Reactant 2

HCID 7498Benzyl Bromide

HCID 69418079HCID 69418079, compound

Product 1

HCID 10126425HCID 10126425, compound

Procedure

Using essentially the same procedure as in Example 1, Step E, but substituting allyl bromide for benzyl bromide, methyl 6-(4-chlorophenyl)-5-(phenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate (500 mg, 1.47 mmol) from Example 1, Step D afforded the desired higher Rf O-alkylation title compound after purification by flash column chromatography on silica gel (eluted with a gradient of 5 to 10% ethyl acetate in hexanes). HPLC/MS: 380 (M+1); Rt=4.7 min. 1HNMR (CDCl3): δ 3.954 (s, 3H), 5.09 (br d, J=5 Hz, 2H), 5.32 (dd, J=1.5 and 10.5 Hz, 1H), 5.45 (br dd, J=1.6 and 18 Hz, 1H), 6.13-6.23 (m, 1H), 7.16-7.21 (m, 2H), 7.22 (d, J=8.6 Hz, 2H), 7.30-7.36 (m, 3H), 7.37 (d, J=8.6 Hz, 2H), 8.246 (s, 1H).

Sources & evidence

ORD record: ord-39801c6b777247e1a012419ffe8b0289
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271266B2

Reaction notes

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