Sodium Carbonate → (R)-(3-methyl-4-(5-(4-(trifluoromethyl)phenyl)pyrido[2,3-d]pyridazin-8-yl)piperazin-1-yl)(phenyl)methanone

HRID 1514401Notes

Reaction equation

HRID 1514401 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:15])[CH2:10][C@H:9]2[CH3:22])=[C:4]2[N:23]=[CH:24][CH:25]=[CH:26][C:3]=12.[F:27][C:28]([F:39])([F:38])[C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:22][C@H:9]1[N:8]([C:5]2[N:6]=[N:7][C:2]([C:32]3[CH:33]=[CH:34][C:29]([C:28]([F:39])([F:38])[F:27])=[CH:30][CH:31]=3)=[C:3]3[CH:26]=[CH:25][CH:24]=[N:23][C:4]=23)[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])[CH2:10]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 57657595(R)-(4-(5-chloropyrido[2,3-d]pyridazin-8-yl)-3-methylpiperazin-1-yl)(phenyl)methanone

Product 1

HCID 25224710(R)-(3-methyl-4-(5-(4-(trifluoromethyl)phenyl)pyrido[2,3-d]pyridazin-8-yl)piperazin-1-yl)(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Using methods described in Example 6, and starting with (R)-(4-(5-chloropyrido[2,3-d]pyridazin-8-yl)-3-methylpiperazin-1-yl)(phenyl)methanone 79 (180 mg, 489 μmol), tetrakis(triphenylphosphine)palladium (283 mg, 245 μmol), 4-trifluoromethylphenylboronic acid (139 mg, 734 μmol), and 2 M sodium carbonate (489 μl, 979 μmol) afforded (R)-(3-methyl-4-(5-(4-(trifluoromethyl)phenyl)pyrido[2,3-d]pyridazin-8-yl)piperazin-1-yl)(phenyl)methanone 84 after chromatographic purification. MS 477.2 (calc'd) 478.1 (M+H, found).

Sources & evidence

ORD record
ord-9175f8decb32467eb4b3a03aaa4e76a4
Source dataset
uspto-grants-2012_07
Patent number
US08222251B2

Reaction notes

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