Acetic Acid → 4-[6-Methoxy-5-(3-methyl-1H-indol-2-yl)-pyridazin-3-yl]-2,6-dimethyl-phenol

HRID 1786696Notes

Reaction equation

Cl[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].S([O-])([O-])(=O)=O.[Mg+2].[OH:15][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([C:23]2[N:28]=[N:27][C:26]([O:29][CH3:30])=[C:25]([C:31](=O)[CH2:32][CH3:33])[CH:24]=2)=[CH:18][C:17]=1[CH3:35].C(O)(=O)C>CC(N(C)C)=O>[CH3:30][O:29][C:26]1[N:27]=[N:28][C:23]([C:19]2[CH:20]=[C:21]([CH3:22])[C:16]([OH:15])=[C:17]([CH3:35])[CH:18]=2)=[CH:24][C:25]=1[C:31]1[NH:4][C:3]2[C:2]([C:32]=1[CH3:33])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

Conditions

Temperature: 140 °C

Procedure

73.4 μl of 2-chloroaniline and 21 mg of anhydrous magnesium sulfate are suspended in 3 ml dimethylacetamide. 100 mg of 1-[6-(4-Hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-propan-1-one and 31.4 mg acetic acid are added and the reaction is degassed with argon. 96 mg of tripotassium phosphate and 35.7 mg of bis(tri-tert-butylphosphine) palladium (0) are added and the reaction is degassed with argon. The reaction is heated to 140° C. for 16 h. The solution is filtered. The product is purified by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid). Yield 35 mg.

Workup

customthe reaction is degassed with argon
addition96 mg of tripotassium phosphate and 35.7 mg of bis(tri-tert-butylphosphine) palladium (0) are added
customthe reaction is degassed with argon
filtrationThe solution is filtered
customThe product is purified by preparative RP-HPLC
washeluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid)

Sources & evidence

ORD record: ord-dfbd9f5c18534ceebd8b86e1288c2370
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507734B2

Reaction notes

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