Tetrahydrofuran → 5-(3,5-Dimethyl-2-phenylethynyl-3H-imidazol-4-yl)-3-methyl-[1,2,4]oxadiazole

HRID 584695노트

반응식

HRID 584695 반응식
Br[C:2]1[N:6]([CH3:7])[C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[N:9]=2)=[C:4]([CH3:14])[N:3]=1.C1COCC1.[C:20]1([C:26]#[CH:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:7][N:6]1[C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[N:9]=2)=[C:4]([CH3:14])[N:3]=[C:2]1[C:27]#[C:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 222717145-(2-bromo-3,5-dimethyl-3H-imidazol-4-yl)-3-methyl-[1,2,4]oxadiazole

생성물 1

HCID 98821075-(3,5-Dimethyl-2-phenylethynyl-3H-imidazol-4-yl)-3-methyl-[1,2,4]oxadiazole수율 55.1%

시약·촉매·용매 2

HCID 11776Triphenylphosphine촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매

실험 절차

To a stirred solution of 5-(2-bromo-3,5-dimethyl-3H-imidazol-4-yl)-3-methyl-[1,2,4]oxadiazole (0.52 g, 2.02 mmol) in THF (10 mmol) was added at RT bis(triphenyl-phosphin)palladium(II)chloride (71 mg, 0.1 mmol), phenylacetylene (0.31 g, 3.03 mmol), triphenylphosphine (27 mg, 0.1 mmol) and triethylamine (0.61 g, 6.07 mmol). Through the reaction mixture was bubbled argon for 10 min and stirring was continued at 55° C. for 16 h. The reaction mixture was poured into water (50 ml) and extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with brine (40 ml), dried (MgSO4) and evaporated to give the crude product as yellow oil (0.81 g). Purification by column chromatography on silica gel (ethyl acetate/toluene 5:1) gave the title compound (0.31 g, 55%) as a light yellow solid, m.p. 137° C. and MS: m/e=278.1 (M+).

후처리

  1. customThrough the reaction mixture was bubbled argon for 10 min
  2. additionThe reaction mixture was poured into water (50 ml)
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. washThe combined organic layers were washed with brine (40 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give the crude product as yellow oil (0.81 g)
  8. customPurification by column chromatography on silica gel (ethyl acetate/toluene 5:1)

출처 및 근거

ORD 기록
ord-5446198aa58045f9915edb33631233b5
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06927232B2

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