1-Ethynyl-4-methoxybenzene → 4-chloro-3-(3-methoxyphenyl)-5-(4-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-c]pyridazine

HRID 1525385Notes

Reaction equation

HRID 1525385 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]2[N:14]([CH3:24])[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3Cl)[C:3]=12.[CH3:25][O:26]C1C=C(C=CC=1)C(CC#N)=O.[CH3:38][O:39]C1C=CC(C#C)=CC=1>>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([O:26][CH3:25])=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]2[N:14]([CH3:24])[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:39][CH3:38])[CH:18]=3)[C:3]=12

Participants

4

Reactant 3

HCID 2510201-Ethynyl-4-methoxybenzeneHCID 5847163-(3-Methoxyphenyl)-3-oxopropanenitrileHCID 665764824-chloro-3-(2-chlorophenyl)-1-methyl-5-phenyl-1H-pyrazolo[3,4-c]pyridazine

Product 1

HCID 665765594-chloro-3-(3-methoxyphenyl)-5-(4-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-c]pyridazine

Procedure

Compound 15 was synthesised following similar procedures outlined in Example 1 (Compound 37), using 3-methoxybenzoylacetonitrile instead of 2-chlorobenzoyl acetonitrile in Step 1 and 4-methoxyphenyl acetylene instead of phenyl acetylene in Step 4.

Sources & evidence

ORD record
ord-a69738c2939a43ac9b35708732ea6766
Source dataset
uspto-grants-2015_07
Patent number
US09079909B2

Reaction notes

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