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

HRID 1514399Notes

Reaction equation

HRID 1514399 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.[OH:27][CH2:28][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>[OH:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:2]2[N:7]=[N:6][C:5]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[O:15])[CH2:10][C@H:9]3[CH3:22])=[C:4]3[N:23]=[CH:24][CH:25]=[CH:26][C:3]=23)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 57657595(R)-(4-(5-chloropyrido[2,3-d]pyridazin-8-yl)-3-methylpiperazin-1-yl)(phenyl)methanone

Product 1

HCID 25224708(R)-(4-(5-(4-(hydroxymethyl)phenyl)pyrido[2,3-d]pyridazin-8-yl)-3-methylpiperazin-1-yl)(phenyl)methanoneYield 57%

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), 4-(hydroxymethyl)phenylboronic acid (112 mg, 734 μmol), tetrakis(triphenylphosphine)palladium (28 mg, 24 μmol), and 2 M sodium carbonate (489 μl, 979 μmol) yielded (R)-(4-(5-(4-(hydroxymethyl)phenyl)pyrido[2,3-d]pyridazin-8-yl)-3-methylpiperazin-1-yl)(phenyl)methanone 82 (122 mg, 57% yield) after chromatographic purification. MS 439.2 (calc'd) 440.2 (M+H, found).

Sources & evidence

ORD record
ord-086efec032b1470e81fd6dac49fb54d4
Source dataset
uspto-grants-2012_07
Patent number
US08222251B2

Reaction notes

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