2,5-Dihydrofuran → N-(4-(3-(2,3-Dihydrofuran-2-YL)pyridin-2-yloxy)phenyl)benzo[D]thiazol-2-amine

HRID 1880156

Reaction equation

HRID 1880156 reaction equation
I[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[S:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.CN(C1CCCCC1)C1CCCCC1.[O:39]1[CH2:43][CH:42]=[CH:41][CH2:40]1>O1CCOCC1.CO.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[O:39]1[CH:40]=[CH:41][CH2:42][CH:43]1[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[S:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 155702,5-DihydrofuranHCID 24210N-Methyl dicyclohexylamineHCID 59327141N-(4-(3-Iodopyridin-2-yloxy)phenyl)benzo[D]thiazol-2-amine

Product 1

HCID 59326959N-(4-(3-(2,3-Dihydrofuran-2-YL)pyridin-2-yloxy)phenyl)benzo[D]thiazol-2-amine

Reagents, catalysts & solvents 3

HCID 178418851HCID 178418851, compoundCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-(4-(3-iodopyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine (0.403 g, 0.905 mmol), N-methyldicyclohexylamine (0.400 mL, 1.886 mmol, Aldrich), bis(tri-tert-butylphosphine)palladium (0) (0.045 g, 0.088 mmol, Strem) and 2,5-dihydrofuran (0.500 mL, 6.78 mmol, Aldrich) in 5 mL of dioxane was capped under an atmosphere of argon and stirred at rt for 3 h and then heated at 45° C. overnight. The reaction mixture was diluted with MeOH, evaporated onto silica gel and purified by flash chromatography (Isco, (40 gram)) eluting with 2M NH3 in MeOH:CH2Cl2 (0:1→3:97) to give a white amorphous solid. MS (ESI, pos. ion) m/z: 386.0 (M+1).

Workup

  1. customwas capped under an atmosphere of argon
  2. temperatureheated at 45° C. overnight
  3. customevaporated onto silica gel
  4. custompurified by flash chromatography (Isco, (40 gram))
  5. washeluting with 2M NH3 in MeOH:CH2Cl2 (0:1→3:97)
  6. customto give a white amorphous solid

Sources & evidence

ORD record
ord-0b75d648e2394da9a601f999ad6e9a57
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Linked notes

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