Sodium Carbonate → HCID 25016338, compound

HRID 1878740Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5](=[O:23])[N:6]([CH2:8][CH2:9][O:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[N:14]=[CH:13][CH:12]=2)[N:7]=1.[S:24]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C([O-])(O)=O.[Na+].CCOC(C)=O>[CH3:22][O:21][C:17]1[CH:16]=[C:15]2[C:20]([C:11]([O:10][CH2:9][CH2:8][N:6]3[C:5](=[O:23])[CH:4]=[CH:3][C:2]([C:26]4[CH:27]=[CH:28][S:24][CH:25]=4)=[N:7]3)=[CH:12][CH:13]=[N:14]2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 6-chloro-2-(2-(7-methoxyquinolin-4-yloxy)ethyl)pyridazin-3(2H)-one (0.090 g, 0.27 mmol) and 3-thiopheneboronic acid (0.069 g, 0.54 mmol) in 4 mL of dioxane was added 1 mL of 1N Na2CO3 followed by 30 mg of FibreCat, in a microwave vial. The reaction was heated to 120° C. for 30 minutes. The mixture was then diluted with 40 mL of NaHCO3 and 60 mL of EtOAc. The organic phase was separated, washed with 30 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtAOc to 10% MeOH/EtOAc) to give a white solid (0.074 g, 72% yield). MS (ESI pos. ion) m/z (MH+): 380.1. Calc'd Exact Mass for C20H17N3O3S: 379.1.

Workup

customThe organic phase was separated
washwashed with 30 mL of brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (EtAOc to 10% MeOH/EtOAc)

Sources & evidence

ORD record: ord-fdd1f907aea84019b9c7e26a2c0bd03b
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314087B2

Reaction notes

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