Triethylamine → HCID 86677039、化合物

HRID 927126ノート

反応式

HRID 927126 の反応式
[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12]([CH:23]=[CH2:24])=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[F:47][C:48]1[CH:53]=[C:52](I)[CH:51]=[CH:50][C:49]=1[C:55]([F:58])([F:57])[F:56].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12](/[CH:23]=[CH:24]/[C:52]2[CH:51]=[CH:50][C:49]([C:55]([F:57])([F:58])[F:56])=[C:48]([F:47])[CH:53]=2)=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 27373432-Fluoro-4-iodo-1-(trifluoromethyl)benzeneHCID 86677037HCID 86677037、化合物2 回

生成物 1

HCID 86677039HCID 86677039、化合物収率 67%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

A vessel containing 3,4-bis(benzyloxy)-6-ethenylpyridazine (Intermediate 78, 1.09 g, 3.42 mmol), tris-(2-methylphenyl)phosphane (0.208 g, 0.685 mmol), 2-fluoro-4-iodo-1-(trifluoromethyl)benzene (1.191 g, 4.11 mmol) and palladium(II) acetate (0.038 g, 0.171 mmol) was evacuated and acetonitrile (10 ml) and triethylamine (9.07 ml, 65.1 mmol) were added in vacuo and then the mixture was flushed with nitrogen. The reaction was then heated in the microwave at 80° C. for 4 hours and, upon cooling, was diluted with dichloromethane and washed with saturated aqueous ammonium chloride solution. The organics were dried (MgSO4), filtered and solvent removed in vacuo to give a brown oil which was purified by column chromatography (silica, eluting with 30-100% dichloromethane in petrol) to yield 3,4-bis(benzyloxy)-6-[(E)-2-[3-fluoro-4-(trifluoromethyl)phenyl]ethenyl]pyridazine (1.1 g, 2.29 mmol, 67% yield).

後処理

  1. customwas evacuated
  2. customthe mixture was flushed with nitrogen
  3. temperatureupon cooling
  4. additionwas diluted with dichloromethane
  5. washwashed with saturated aqueous ammonium chloride solution
  6. dry with materialThe organics were dried (MgSO4)
  7. filtrationfiltered
  8. customsolvent removed in vacuo
  9. customto give a brown oil which
  10. customwas purified by column chromatography (silica, eluting with 30-100% dichloromethane in petrol)

出典と根拠

ORDレコード
ord-1c5649e27ecb403a8866a17faeb629bb
出典データセット
uspto-grants-2016_03
特許番号
US09290456B2

反応ノート

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