Potassium Carbonate → {2-[(2,3-Dimethoxy-quinoxalin-6-ylmethyl)-amino]-5-prop-2-ynyloxy-phenyl}-(4-isopropyl-phenyl)-methanone

HRID 641814Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]#[CH:11])=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=1)=[O:13].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[N:37]=[C:36]([O:41][CH3:42])[C:35]([O:43][CH3:44])=[N:34]2>O1CCOCC1.O>[CH3:42][O:41][C:36]1[C:35]([O:43][CH3:44])=[N:34][C:33]2[C:38](=[CH:39][CH:40]=[C:31]([CH2:30][NH:1][C:2]3[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]#[CH:11])=[CH:4][C:3]=3[C:12]([C:14]3[CH:15]=[CH:16][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:18][CH:19]=3)=[O:13])[CH:32]=2)[N:37]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 82 mg (0.280 mmol) (2-amino-5-propargyloxy-phenyl)-(4-isopropyl-phenyl)-methanone in 3 ml dioxane is added 193 mg (1.40 mmol) potassium carbonate and 119 mg (0.419 mmol) 6-Bromomethyl-2,3-dimethoxy-quinoxalin. The mixture is stirred at 80° C. for two days, diluted with water and extracted with CH2Cl2. Purification of the crude product by chromatography (ethyl acetate/hexanes 1:1) affords a yellow oil.

Workup

extractionextracted with CH2Cl2
customPurification of the crude product by chromatography (ethyl acetate/hexanes 1:1)
customaffords a yellow oil

Sources & evidence

ORD record: ord-57d53e03261446d4bcfde7573313cff9
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696216B2

Reaction notes

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