Diethyl Ether → HCID 69995874, compound

HRID 1468005Notes

Reaction equation

HRID 1468005 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Li]CCCC.CCOCC.I[C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2>C1COCC1.[Cl-].[Cl-].[Zn+2]>[NH:22]1[C:23]2[C:19](=[CH:18][C:17]([C:2]3[O:1][CH:5]=[CH:4][N:3]=3)=[CH:25][CH:24]=2)[CH:20]=[CH:21]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 9255OxazoleHCID 27823135-Iodo-1H-indoleHCID 178418339Butyllithium

Product 1

HCID 69995874HCID 69995874, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution oxazole (0.1 g, 1.45 mmol) in anhydrous THF (3 mL), n-BuLi (1.6 mL, 1.6 mmol) was added at −78° C. and stirred for 30 minutes. The reaction mixture was brought to 0° C., ZnCl2.Et2O (4.35 mL, 4.35 mmol) was added and stirred for 1 h. 5-iodo-1H-indole (0.352 g, 1.45 mmol) and (Ph3P)PdCl2 (0.050 g, 0.072 mmol) were added and stirred at 80° C. for 1 h. The reaction mixture was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residue was purified by flash column chromatography to give 2-(1H-indol-5-yl)oxazole (0.060 g, 22%); MS: 185.0 (M+1).

Workup

  1. customwas brought to 0° C.
  2. stirringstirred for 1 h
  3. stirringstirred at 80° C. for 1 h
  4. customThe reaction mixture was quenched with water
  5. extractionthe mixture was extracted with ethyl acetate
  6. concentrationThe organic layer was concentrated in vacuo
  7. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-0dba0f9f3e7b407ea20901d00e98e31b
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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