Dichloromethane → HCID 44125127, compound

HRID 1162484Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12](=[O:14])[CH3:13])[N:10]=2)[N:7]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][C:22]=1[O:23][CH3:24].ClCCl.C(=O)([O-])[O-].[K+].[K+]>Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O.COCCOC>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([CH:8]=[C:9]([NH:11][C:12](=[O:14])[CH3:13])[N:10]=3)[N:7]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]

Participants

Conditions

Temperature: 100 °C

Procedure

To a 10-mL, reaction vial was added N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide (0.108 g, 0.51 mmol), 3,4-dimethoxyphenylboronic acid (0.112 g, 0.61 mmol, Alfa Aesar, Ward Hill, Mass.), [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium, complex with dichloromethane (31 mg, 0.038 mmol), potassium carbonate (0.213 g, 1.54 mmol), DME (3 mL), and water (1 mL). The vial was sealed and purged with nitrogen for several minutes. The mixture was stirred at 100° C. for 1 h and then allowed to cool to room temperature. The organic phase was taken and the solvents eliminated under vacuum. Purification by silica gel chromatography (4 to 6% MeOH/CH2Cl2) afforded the title compound as an off-white solid. MS (ESI positive ion) m/z: 313 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 10.86 (s, 1H), 8.26 (s, 1H), 8.00 (d, J=9.6 Hz, 1H), 7.78 (d, J=9.6 Hz, 1H), 7.66-7.57 (m, 2H), 7.11 (d, J=9.0 Hz, 1H), 3.88 (s, 3H), 3.84 (s, 3H), 2.11 (s, 3H).

Workup

customTo a 10-mL, reaction
customThe vial was sealed
custompurged with nitrogen for several minutes
temperatureto cool to room temperature
customPurification by silica gel chromatography (4 to 6% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-980726f376df4d7a8e0643a17ff4ca60
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820665B2

Reaction notes

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