Hydrochloric Acid → 4-(1H-Indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one

HRID 2234063Notes

Reaction equation

C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[CH:22]=[C:21]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[N:20]=[N:19][C:18]=1[O:29]C)=O)(C)(C)C.C[Si](C)(C)Cl.Cl.CN(C)C=O>C(#N)C.O1CCOCC1>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[C:18](=[O:29])[NH:19][N:20]=[C:21]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[CH:22]=1

Participants

Conditions

Temperature: 60 °C

Procedure

25 mg of 2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester, 7.4 mg trimethylchlorosilane and 11.3 mg KI dissolved in 1 ml of acetonitril are stirred for 2 h at 60° C. Subsequently 0.5 ml of a 4N solution of hydrochloric acid in dioxane is added and stirred for 2 h at room temperature. The solution is diluted into DMF (dimethylformamide)/water and directly purified by HPLC (high performance liquid chromatography) on a RP18 (reversed phase 18) column giving 4.5 mg 4-(1H-Indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one.

Workup

stirringstirred for 2 h at room temperature
customdirectly purified by HPLC (high performance liquid chromatography) on a RP18 (reversed phase 18) column

Sources & evidence

ORD record: ord-0fbaf4121e4b42eeb93af6374fba7dde
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709466B2

Reaction notes

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