Nitrogen → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(2-methyl-benzo[b]thiophen-3-yl)-imidazo[1,2-b]pyridazine

HRID 226076Notes

Reaction equation

[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([CH:13]=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].Br[C:18]1[C:19]2[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=2[S:21][C:22]=1[CH3:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].N#N>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:18]3[C:19]4[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=4[S:21][C:22]=3[CH3:23])=[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

217 mg of 8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (11.0 mmol), 227 mg of 3-bromo-2-methyl-benzo[b]thiophene (1.0 mmol), 26.2 mg of triphenylphosphine (0.1 mmol) and 650 mg of cesium carbonate (2.0 mmol) are placed into a reaction vial with 3 ml of dry DMF. N2 gas is bubbled in for 10 min and 34 mg of palladium acetate (0.05 mmol) is added. The reaction vial is capped with a Teflon cap and heated at 130° C. overnight. The reaction mixture is concentrated and applied onto a silica-gel chromatography column (Hexane:AcOEt:2M NH3 in MeOH=10:2:1) to give the title compound 119 mg (33%). mass spectrum (m/e): 364; 1H-NMR (CDCl3): 7.86 (m, 1H), 7.31 (m, 3H), 6.72 (s, 1H), 3.44 (m, 1H), 2.47 (s, 3H), 2.42 (s, 3H), 1.90 (m, 4H), 0.95 m, 6H) ppm.

Workup

additionis added
customThe reaction
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concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record: ord-ccd6ff5628d94ffa97ca4706f481bfc4
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557103B2

Reaction notes

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