Ethyl bromopyruvate → 3-[4-(2-Ethoxycarbonylimidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

HRID 357027Notes

Reaction equation

[NH2:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:17](=[O:18])[CH2:16][S:15][C:14]2=[O:19])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:21][C:22](=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24]>>[CH2:26]([O:25][C:23]([C:22]1[N:1]=[C:2]2[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]3[C:17](=[O:18])[CH2:16][S:15][C:14]3=[O:19])=[CH:6][CH:5]=[CH:4][N:3]2[CH:21]=1)=[O:24])[CH3:27]

Participants

Reactant 2

HCID 66144Ethyl bromopyruvate

HCID 189367033-[4-(2-Aminopyridin-3-yloxy)butyl]thiazolidine-2,4-dione

Product 1

HCID 189366473-[4-(2-Ethoxycarbonylimidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

Procedure

Using 5.69 g (20 mmol) of 3-[4-(2-aminopyridin-3-yloxy)butyl]thiazolidine-2,4-dione and 2.51 ml (20 mmol) of ethyl bromopyruvate, the same procedure as in Reference Example 27 was followed, to yield 3.28 g (43.5%, light orange oily substance) of the desired product.

Sources & evidence

ORD record: ord-d19355884de24dc5bb4e9965ec0ad616
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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