Carbon Tetrachloride → HCID 58966940、化合物

HRID 1948210

反応式

HRID 1948210 の反応式
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:29]=[CH:30][C:31](=[O:38])[N:32]([CH2:34][C:35]([OH:37])=O)[CH:33]=2)=[CH:24][CH:23]=1.[NH2:39][C:40]1[CH:45]=[C:44]([F:46])[CH:43]=[CH:42][C:41]=1O.CCN(CC)CC.C(Cl)(Cl)(Cl)Cl>C(#N)C.N1C=CC=CC=1>[F:46][C:44]1[CH:43]=[CH:42][C:41]2[O:37][C:35]([CH2:34][N:32]3[CH:33]=[C:28]([C:25]4[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[CH:27][CH:26]=4)[CH:29]=[CH:30][C:31]3=[O:38])=[N:39][C:40]=2[CH:45]=1

参加物

7

反応物 5

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 27359172-Amino-4-fluorophenolHCID 694409442-(5-(4-methoxyphenyl)-2-oxopyridin-1(2H)-yl)acetic acid

生成物 1

HCID 58966940HCID 58966940、化合物収率 17.1%

試薬・触媒・溶媒 1

HCID 21959178Acetonitrile pyridine溶媒2 回

実験手順

According to Scheme 10 Method A: A solution of PPh3 (3 eq, 1.04 mmol, 0.27 g) in 1:1 acetonitrile/pyridine (3 mL) was added dropwise over a period of 1 hour to a mixture of 2-(5-(4-methoxyphenyl)-2-oxopyridin-1(2H)-yl)acetic acid (1 eq, 0.35 mmol, 0.09 g, Example 14 Step 2), 2-amino-4-fluorophenol (1 eq, 0.35 mmol, 0.04 g), Et3N (3 eq, 1.04 mmol, 0.15 mL) and CCl4 (4 eq, 1.39 mmol, 0.13 mL) in 1:1 mixture of acetonitrile/pyridine (3 mL). The reaction mixture was stirred at room temperature for 2 days. The solvent was removed under reduced pressure and the residue was dissolved in CH2Cl2 and NH4OH. The aqueous phase was extracted 3 times with CH2Cl2. The combined organic fractions were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 15 g SiO2) using CH2Cl2/AcOEt 90/10 as eluent to afford 1-((5-fluorobenzo[d]oxazol-2-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (0.06 mmol, 0.02 g, 16%) as a brown solid.

後処理

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. extractionThe aqueous phase was extracted 3 times with CH2Cl2
  4. washThe combined organic fractions were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 15 g SiO2)

出典と根拠

ORDレコード
ord-565ff666eb6942fca9f8695a9a6b90b7
出典データセット
uspto-grants-2013_03
特許番号
US08399493B2

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