HCID 54742342, compound → HCID 68616465, compound

HRID 1887334Notes

Reaction equation

HRID 1887334 reaction equation
C([C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[CH2:10]Br)C.[OH:12][C:13]1[CH:18]=[CH:17][N:16]([C:19]2[S:20][C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:22]([CH3:24])[N:23]=2)[C:15](=[O:30])[CH:14]=1>>[F:9][C:7]1[CH:8]=[CH:3][C:4]([CH2:10][O:12][C:13]2[CH:18]=[CH:17][N:16]([C:19]3[S:20][C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:22]([CH3:24])[N:23]=3)[C:15](=[O:30])[CH:14]=2)=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 54742342HCID 54742342, compoundHCID 68618099HCID 68618099, compound

Product 1

HCID 68616465HCID 68616465, compoundYield 70%

Procedure

Following the procedure as described in Example 17, making variations only as required to use ethyl 1-(bromomethyl)-4-fluorobenzene in place of 2-(bromomethyl)-5-(trifluoromethyl)furan to react with ethyl 2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylate, the title compound was obtained as a colorless solid in 70% yield: mp 214-217° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.70 (d, J=8.1 Hz, 1H), 7.42-7.34 (m, 2H), 7.12-7.04 (m, 2H), 6.20 (dd, J=8.1, 2.7 Hz, 1H), 6.07 (d, J=2.7 Hz, 1H), 5.01 (s, 2H), 4.32 (q, J=7.1 Hz, 2H), 2.68 (s, 3H), 1.36 (t, J=7.1 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 167.1, 164.5, 162.8, 161.2, 156.5, 155.6, 131.5, 130.4, 129.8, 119.8, 115.9, 103.9, 97.4, 70.1, 61.9, 17.3, 14.3; MS (ES+) m/z 389.2 (M+1).

Sources & evidence

ORD record
ord-ad7f11dc04a348f9b6bd186276a5235d
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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