Hexane → HCID 86621041, compound

HRID 226085Notes

Reaction equation

HRID 226085 reaction equation
[Br:1][C:2]1[C:6]2=[N:7][C:8]([Cl:11])=[CH:9][CH:10]=[C:5]2[S:4][CH:3]=1.[Li]CCCC.CCCCCC.[CH2:23]([CH:25]([C:28]1[C:29]2[N:30]([C:35](I)=[C:36]([CH3:38])[N:37]=2)[N:31]=[C:32]([CH3:34])[CH:33]=1)[CH2:26][CH3:27])[CH3:24]>C1COCC1.[Cl-].[Cl-].[Zn+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:1][C:2]1[C:6]2=[N:7][C:8]([Cl:11])=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[C:35]1[N:30]2[N:31]=[C:32]([CH3:34])[CH:33]=[C:28]([CH:25]([CH2:23][CH3:24])[CH2:26][CH3:27])[C:29]2=[N:37][C:36]=1[CH3:38].[Cl:11][C:8]1[N:7]=[C:6]2[C:2]([C:35]3[N:30]4[N:31]=[C:32]([CH3:34])[CH:33]=[C:28]([CH:25]([CH2:23][CH3:24])[CH2:26][CH3:27])[C:29]4=[N:37][C:36]=3[CH3:38])=[CH:3][S:4][C:5]2=[CH:10][CH:9]=1

Participants

9

Reactant 4

HCID 8058HexaneHCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazineHCID 714643393-Bromo-5-chlorothieno[3,2-b]pyridineHCID 178418339Butyllithium

Product 2

HCID 86621041HCID 86621041, compoundYield 3%HCID 86621042HCID 86621042, compoundYield 2%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

248 g of 3-Bromo-5-chloro-thieno[3,2-b]pyridine (1.0 mol) is dissolved in 2.0 l of dry THF and cooled to −78° C. 0.4 l of n-BuLi 2.5M in hexane (1.0 mol) is added slowly and stirred at −78° C. for 15 in. 2.0 l of 0.5M ZnCl2 in THF (1.0 mol) is added and stirred at room temperature for 20 in. 343 g of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (1.0 mol) and 37 g of PdCl2(dppf) (0.05 mol) are added and the reaction vial is capped with a Teflon cap. The vial is heated at 80° C. overnight. The reaction mixture is filtered and applied onto a silica-gel chromatography column (1st column; hexane AcOEt=10:1, 2nd column; CH3CN:CH2Cl2:Hexane=1:5:4) to give 16 mg of 3-(3-bromo-5-chloro-thieno[3,2-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (3%) and 9 mg of 3-(5-chloro-thieno[3,2-b]pyridin-3-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (2%).

Workup

  1. stirringstirred at room temperature for 20 in
  2. customthe reaction
  3. customcap
  4. temperatureThe vial is heated at 80° C. overnight
  5. filtrationThe reaction mixture is filtered

Sources & evidence

ORD record
ord-1baf341a6e8f4cabaadffd55d6874970
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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