Ethyl bromopyruvate → 8-Iodo-5-phenyl-imidazo[1,2-a]quinoline-2-carboxylic acid ethyl ester

HRID 2075666Notes

Reaction equation

[I:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][C:8]([NH2:12])=[N:9]2)=[CH:4][CH:3]=1.Br[CH2:20][C:21](=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)(O)[O-].[Na+]>CCO>[CH2:25]([O:24][C:22]([C:21]1[N:12]=[C:8]2[CH:7]=[C:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:5]3[C:10](=[CH:11][C:2]([I:1])=[CH:3][CH:4]=3)[N:9]2[CH:20]=1)=[O:23])[CH3:26]

Participants

Conditions

Temperature: 80 °C

Procedure

7-Iodo-4-phenyl-quinolin-2-ylamine (100 mg, 0.29 mmol), ethyl bromopyruvate (0.05 mL, 0.43 mmol), and sodium bicarbonate (22 mg, 0.58 mmol) were dissolved in EtOH (2 mL) and heated to 80° C. for 3 hours. The mixture was concentrated and purified by silica gel chromatography (30% EtOAc in hexanes) to give the desired product, 1v.

Workup

concentrationThe mixture was concentrated
custompurified by silica gel chromatography (30% EtOAc in hexanes)

Sources & evidence

ORD record: ord-bc4650ef960048d5aee8ceba48aeb397
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919621B2

Reaction notes

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