Hexane → HCID 68858331, compound

HRID 226074Notes

Reaction equation

[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[S:4][CH:3]=1.[Li]CCCC.CCCCCC.[CH2:22]([CH:24]([C:27]1[C:28]2[N:29]([C:34](I)=[C:35]([CH3:37])[N:36]=2)[N:30]=[C:31]([CH3:33])[CH:32]=1)[CH2:25][CH3:26])[CH3:23]>C1COCC1.[Cl-].[Cl-].[Zn+2]>[CH2:22]([CH:24]([C:27]1[C:28]2[N:29]([C:34]([C:3]3[S:4][C:5]4=[CH:6][N:7]=[CH:8][CH:9]=[C:10]4[C:2]=3[CH3:1])=[C:35]([CH3:37])[N:36]=2)[N:30]=[C:31]([CH3:33])[CH:32]=1)[CH2:25][CH3:26])[CH3:23]

Participants

Conditions

Temperature: -78 °C

Procedure

149 mg of 3-Methyl-thieno[2,3-c]pyridine (1.0 mmol) is dissolved in 3.0 ml of dry THF and cooled to −78° C. 0.48 ml of n-BuLi 2.5M in hexane (1.2 mmol) is added at −78° C. and stirred at −78° C. for 10 min and room temperature for 10 min. The reaction vessel is cooled to −78° C. again and 2.6 ml of 0.5M ZnCl2 in THF (1.3 mmol) is added at −78° C. and stirred at room temperature for 15 min. 274 mg of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (2151431) (0.8 mmol) and 41 mg of PdCl2(pddf) (0.05 mmol) are added and the tube is capped. The tube is heated at 80° C. for 3 days. The reaction is quenched by NH4Claq. and extracted by CH2Cl2, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane:AcOEt:2 M NH3 in MeOH=20:4:1) to give 131 mg of the title compound. Yield 45%. mass spectrum (m/e): 365 (M+1).

Workup

temperatureThe reaction vessel is cooled to −78° C. again
stirringstirred at room temperature for 15 min
customthe tube is capped
temperatureThe tube is heated at 80° C. for 3 days
customThe reaction is quenched by NH4Claq
extractionand extracted by CH2Cl2
dry with materialdried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-bfe8851f79074039b54687e34df0bb48
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557103B2

Reaction notes

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