Potassium Carbonate → HCID 90406846, compound

HRID 2277543Notes

Reaction equation

HRID 2277543 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[C:10]([C:12]([NH2:14])=[O:13])[CH:9]=[CH:8][N:7]=2)[N:3]=[CH:2]1.Br[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][CH2:16][N:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[C:10]([C:12]([NH2:14])=[O:13])[CH:9]=[CH:8][N:7]=2)[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27569631-(2-Bromoethyl)-2-chlorobenzeneHCID 178513687HCID 178513687, compound

Product 1

HCID 90406846HCID 90406846, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(1H-imidazol-4-yl)pyridine-4-carboxamide (400 mg, 2.13 mmol, PREPARATION 7), 1-(2-bromo-ethyl)-2-chloro-benzene (557 mg, 2.55 mmol) and K2CO3 (587 mg, 4.26 mmol) in DMF (10 mL) was stirred overnight at 80° C. LC/MS showed the reaction was completed. It was then purified by flash column chromatography to give the title compound (228 mg, 33%) as a yellow solid. [M+H] Calc'd for C17H15ClN4O, 327. Found, 327.

Workup

  1. customIt was then purified by flash column chromatography

Sources & evidence

ORD record
ord-0d996e648cba457984cc8962e1ce3557
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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