Sodium Carbonate → HCID 25224707, compound

HRID 1514398Notes

Reaction equation

HRID 1514398 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:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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[C:4]3[CH:23]=[CH:24][CH:25]=[N:26][C:3]=3[C:2]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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 66827Phenylboronic AcidHCID 57657611HCID 57657611, compound

Product 1

HCID 25224707HCID 25224707, compoundYield 77%

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 80 (68 mg, 185 μmol), tetrakis(triphenylphosphine)palladium (11 mg, 9 μmol), phenylboronic acid (34 mg, 277 μmol), and 2 M sodium carbonate (185 μl, 370 μmol) yielded (R)-(3-methyl-4-(8-phenylpyrido[3,2-d]pyridazin-5-yl)piperazin-1-yl)(phenyl)methanone 81 (58 mg, 77% yield) after chromatographic purification. MS 409.2 (calc'd) 410.2 (M+H, found).

Sources & evidence

ORD record
ord-f38cb6f575d746588e1a35007480ada4
Source dataset
uspto-grants-2012_07
Patent number
US08222251B2

Reaction notes

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