Sodium Methoxide → 8-(1-Ethyl-propyl)-3-(3-methoxy-thieno[3,2-b]pyridin-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

HRID 226080Notes

Reaction equation

HRID 226080 reaction equation
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[C:11]1[N:15]2[N:16]=[C:17]([CH3:25])[CH:18]=[C:19]([CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[C:14]2=[N:13][C:12]=1[CH3:26].[CH3:27][O-:28].[Na+]>[Cu]I.CO>[CH2:21]([CH:20]([C:19]1[C:14]2[N:15]([C:11]([C:3]3[S:4][C:5]4[C:6](=[N:7][CH:8]=[CH:9][CH:10]=4)[C:2]=3[O:28][CH3:27])=[C:12]([CH3:26])[N:13]=2)[N:16]=[C:17]([CH3:25])[CH:18]=1)[CH2:23][CH3:24])[CH3:22]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 577526393-(3-Bromo-thieno[3,2-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

Product 1

HCID 577525918-(1-Ethyl-propyl)-3-(3-methoxy-thieno[3,2-b]pyridin-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazineYield 45%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

50 mg of 3-(3-Bromo-thieno[3,2-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.12 mmol) and 13 mg of sodium methoxide (0.24 mmol) and 22 mg of copper (I) iodide (0.12 mmol) are placed into 4 ml reaction vial with 3.0 ml of dry MeOH. The reaction vial is capped with a Teflon cap and heated at 120° C. overnight. The reaction mixture is filtered, and water and CH2Cl2 are added. The separated CH2Cl2 is dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (1st column; Hexane:AcOEt:2M NH3 in MeOH=20:4:1, 2nd column; CH2Cl2:Hexane:Acetnitrile=5:4:1) to give the title compound 20 mg (45%). mass spectrum (m/e): 381; 1H-NMR (CDCl3): 8.72 (m, 1H), 8.10 (m, 1H), 7.29 (dd, 1H, J=4.6 Hz, 8.3 Hz), 6.72 (s, 1H), 4.03 (s, 3H), 3.34 (m, 1H), 2.55 (s, 3H), 2.54 (s, 3H), 1.84 (m, 4H), 0.88 (t, 6H, J=7.6 Hz) ppm.

Workup

  1. customThe reaction
  2. customcap
  3. filtrationThe reaction mixture is filtered
  4. additionwater and CH2Cl2 are added
  5. dry with materialThe separated CH2Cl2 is dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-8d33ba9f857e444ba03fcd609030cb20
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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