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

HRID 1514402Notes

Reaction equation

HRID 1514402 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.C(=O)([O-])[O-].[Na+].[Na+].[C:33]([C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)#[N:34]>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>[C:14]([N:11]1[CH2:12][CH2:13][N:8]([C:5]2[N:6]=[N:7][C:2]([C:38]3[CH:39]=[CH:40][C:35]([C:33]#[N:34])=[CH:36][CH:37]=3)=[C:3]3[CH:26]=[CH:25][CH:24]=[N:23][C:4]=23)[C@H:9]([CH3:22])[CH2:10]1)(=[O:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 57657595(R)-(4-(5-chloropyrido[2,3-d]pyridazin-8-yl)-3-methylpiperazin-1-yl)(phenyl)methanone

Product 1

HCID 25224711(R)-4-(8-(4-benzoyl-2-methylpiperazin-1-yl)pyrido[2,3-d]pyridazin-5-yl)benzonitrileYield 32%

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 (360 mg, 979 mmol), 2 M sodium carbonate (979 μl, 196 mmol), 4-cyanophenylboronic acid (216 mg, 1.47 mmol), and tetrakis(triphenylphosphine)palladium (57 mg, 49 μmol) afforded (R)-4-(8-(4-benzoyl-2-methylpiperazin-1-yl)pyrido[2,3-d]pyridazin-5-yl)benzonitrile 85 (138 mg, 32% yield) after chromatographic purification. MS 434.2 (calc'd) 435.1 (M+H, found).

Sources & evidence

ORD record
ord-377264d2ac5c443e9d991cf70af47b23
Source dataset
uspto-grants-2012_07
Patent number
US08222251B2

Reaction notes

Loading…