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

HRID 584695ノート

反応式

HRID 584695 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11776Triphenylphosphine触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-5446198aa58045f9915edb33631233b5
出典データセット
uspto-grants-2005_08
特許番号
US06927232B2

反応ノート

読み込み中…