Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate → HCID 24985947, compound

HRID 1887325Notes

Reaction equation

HRID 1887325 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:17]1[S:18][C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:20]([CH3:22])[N:21]=1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:17]2[S:18][C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:20]([CH3:22])[N:21]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylateHCID 36077244-Benzyloxy-2(1H)-pyridone

Product 1

HCID 24985947HCID 24985947, compoundYield 80%

Procedure

Following the procedure as described in Example 12, making variations only as required to use 4-(benzyloxy)pyridin-2(1H)-one in place of 4-phenylpyridin-2-ol to react with ethyl 2-bromo-4-methylthiazole-5-carboxylate, the title compound was obtained as a yellow solid in 80% yield: 1H NMR (300 MHz, CDCl3) δ 8.65 (d, J=7.9 Hz, 1H), 7.42-7.26 (m, 5H), 6.18 (d, J=7.9 Hz, 1H), 6.07 (s, 1H), 5.01 (s, 2H), 4.28 (q, J=7.1 Hz, 1H), 2.65 (s, 3H), 1.32 (t, J=7.1 Hz, 3H); MS (ES+) m/z 371.1 (M+1).

Sources & evidence

ORD record
ord-d698bc12ba554995a8dbba410bc68ddc
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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