Water → HCID 68455996, compound

HRID 2357530Notes

Reaction equation

HRID 2357530 reaction equation
Br[C:2]1[CH:17]=[N:16][C:5]2=[C:6]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[N:7]=[N:8][CH:9]=[C:4]2[CH:3]=1.[CH:18]1([NH:21][C:22](=[O:39])[C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[C:25](B3OC(C)(C)C(C)(C)O3)[CH:24]=2)[CH2:20][CH2:19]1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCO>[CH:18]1([NH:21][C:22](=[O:39])[C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([C:2]3[CH:17]=[N:16][C:5]4=[C:6]([N:10]5[CH2:15][CH2:14][O:13][CH2:12][CH2:11]5)[N:7]=[N:8][CH:9]=[C:4]4[CH:3]=3)[CH:24]=2)[CH2:19][CH2:20]1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 684552693-Bromo-8-(4-morpholinyl)pyrido[2,3-d]pyridazine

Product 1

HCID 68455996HCID 68455996, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

This title compound by heating a mixture of 3-bromo-8-morpholinopyrido[2,3-d]pyridazine (0.033 g, 0.11 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.048 g, 0.16 mmol), sodium carbonate (0.049 g, 0.46 mmol) and trans-dichlorobis(triphenyl-phosphine)palladium (II) (0.011 g, 0.016 mmol) in DME (2.1 mL)/H2O (0.9 mL)/EtOH (0.6 mL) at 80° C. The mixture was cooled to RT, evaporated onto silica gel and purified flash chromatography eluting with 2M NH3 in MeOH:CH2Cl2 (0:1→1:19) to give the title compound as a tan amorphous solid. MS m/z: 390.2 [M+1].

Workup

  1. customevaporated onto silica gel
  2. custompurified flash chromatography
  3. washeluting with 2M NH3 in MeOH:CH2Cl2 (0:1→1:19)

Sources & evidence

ORD record
ord-9448d3aa30a04e24868805b99f93572d
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

Loading…