Sodium Carbonate → HCID 25224889, compound

HRID 1514403Notes

Reaction equation

HRID 1514403 reaction equation
Cl[C:2]1[C:3]2[N:26]=[CH:25][CH:24]=[CH:23][C:4]=2[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])=[N:6][N:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:33][C:34]([F:45])([F:44])[C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1>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[C:4]3[CH:23]=[CH:24][CH:25]=[N:26][C:3]=3[C:2]([C:38]3[CH:39]=[CH:40][C:35]([C:34]([F:45])([F:44])[F:33])=[CH:36][CH:37]=3)=[N:7][N:6]=2)[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 57657611HCID 57657611, compound

Product 1

HCID 25224889HCID 25224889, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Using methods described in Example 6, and starting with (R)-(4-(8-chloropyrido[3,2-d]pyridazin-5-yl)-3-methylpiperazin-1-yl)(phenyl)methanone (180 mg, 489 μmol), 2 M sodium carbonate (489 μl, 979 μmol), tetrakis(triphenylphosphine)palladium (28 mg, 24 μmol), and 4-trifluoromethylphenylboronic acid (139 mg, 734 μmol) afforded (R)-(3-methyl-4-(8-(4-(trifluoromethyl)phenyl)pyrido[3,2-d]pyridazin-5-yl)piperazin-1-yl)(phenyl)methanone 86 after chromatographic purification. MS 477.2 (calc'd) 478.1 (M+H, found).

Sources & evidence

ORD record
ord-755e2c3b82ab45b7af21d26b03ce8adb
Source dataset
uspto-grants-2012_07
Patent number
US08222251B2

Reaction notes

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