Nitrogen → HCID 57932903, compound

HRID 1432567Notes

Reaction equation

[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13](I)=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].[CH3:18][C:19]1[NH:20][CH2:21][S:22][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].N#N>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C=O)C>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:23]3[S:22][CH:21]=[N:20][C:19]=3[CH3:18])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

Conditions

Temperature: 130 °C

Procedure

3.00 g of 8-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (8.74 mmol), 4.32 g of 4-methyl-2H-thiazole (43.6 mmol), 453 mg of triphenylphosphine (1.73 mmol) and 5.85 g of cesium carbonate (18.0 mmol) are placed into the sealed tube with 20 ml of DMF and N2 gas is bubbled in for 40 min. 39 mg of Pd2 dba3 (0.43 mmol) is added and the tube is sealed and heated at 130° C. overnight. The cooled reaction mixture is filtered and applied onto silica-gel column (Hexane→Hexane:AcOEt=3:1) to give 2.12 g of the title compound (77%). 1H-NMR (DMSO-d6) δ 9.215 (s, 1H); 6.993 (s, 1H); 3.079 (m, 1H); 2.480 (s, 3H); 2.439 (s, 3H); 2.302 (s, 3H); 1.824-1.751 (m, 4H); 0.780-0.743 (m, 6H) ppm. MS, ES+=315.2.

Workup

customis bubbled in for 40 min
customthe tube is sealed
customThe cooled reaction mixture
filtrationis filtered

Sources & evidence

ORD record: ord-1c2c5cc4bd6a422a85854b4869cc4e2f
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612067B2

Reaction notes

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