Triethylamine → 2-(5-Methyl-3-phenyl-isoxazol-4-ylethynyl)-pyridine

HRID 1984640

反応式

HRID 1984640 の反応式
I[C:2]1[C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:4][O:5][C:6]=1[CH3:7].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C:50]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][N:53]=1)#[CH:51]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:7][C:6]1[O:5][N:4]=[C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]=1[C:51]#[C:50][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][N:53]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 137268EthynylpyridineHCID 27761504-Iodo-5-methyl-3-phenylisoxazole

生成物 1

HCID 247844462-(5-Methyl-3-phenyl-isoxazol-4-ylethynyl)-pyridine収率 23.1%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 4-iodo-5-methyl-3-phenylisoxazole (285 mg, 1.00 mmol), palladium(II) acetate (7 mg, 0.03 mmol), 1,3-bis(diphenylphosphino)propane (12 mg, 0.03 mmol), triethylamine (348 μL, 2.50 mmol) and 2-ethynylpyridine (131 μL, 1.30 mmol) in N,N-dimethylformamide (2 mL) was evaporated and flushed with argon. Cuprous iodide (4 mg, 0.02 mmol) was added and the reaction mixture was stirred for 3 h at 90° C. before cooling to ambient temperature and separated between aqueous sodium hydroxide (1 M, 30 mL) and ethyl acetate (50 mL). The aqueous layer was extracted with ethyl acetate (50 mL) and washed with aqueous sodium hydroxide (1 M, 30 mL). The combined organic layers were dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 67:33) afforded the title compound (60 mg, 23%) as a light brown solid. MS: m/e=261.2 [M+H]+.

後処理

  1. customwas evaporated
  2. customflushed with argon
  3. temperaturebefore cooling to ambient temperature
  4. customseparated between aqueous sodium hydroxide (1 M, 30 mL) and ethyl acetate (50 mL)
  5. extractionThe aqueous layer was extracted with ethyl acetate (50 mL)
  6. washwashed with aqueous sodium hydroxide (1 M, 30 mL)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. concentrationconcentrated
  9. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 67:33)

出典と根拠

ORDレコード
ord-cfb5c6edebff49b29fea7c3ae5467541
出典データセット
uspto-grants-2009_06
特許番号
US07544704B2

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