Potassium Carbonate → (4-Isopropyl-phenyl)-{5-methoxy-2-[(pyridin-2-ylmethyl)-amino]-phenyl}-methanone

HRID 445157Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Br.BrC[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=1[C:26]([C:28]1[CH:33]=[CH:32][C:31]([CH:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=1)=[O:27]>CC(C)=O.C(OCC)(=O)C>[CH:34]([C:31]1[CH:30]=[CH:29][C:28]([C:26]([C:19]2[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:18]=2[NH:17][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:27])=[CH:33][CH:32]=1)([CH3:36])[CH3:35]

Participants

Conditions

Temperature: 90 °C

Procedure

410 mg (2.97 mmol) potassium carbonate and 150 mg (0.59 mmol) 2-bromoethylpyridine hydrobromide are added to a solution of 160 mg (0.59 mmol) (2-amino-5-methoxy-phenyl)-(4-isopropyl-phenyl)-methanone in 3 ml acetone. The reaction mixture is stirred for 2 days at 90° C., diluted with ethyl acetate and extracted with brine. The organic layer is dried and evaporated. After chromatography (hexane/ethyl acetate) the product is obtained as yellow oil.

Workup

extractionextracted with brine
customThe organic layer is dried
customevaporated
customAfter chromatography (hexane/ethyl acetate) the product is obtained as yellow oil

Sources & evidence

ORD record: ord-1435837fdae74f3696e73de0cb68cde5
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476286B2

Reaction notes

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