Carbon Tetrachloride → HCID 58966940, compound

HRID 1948210

Reaction equation

HRID 1948210 reaction equation
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

Participants

7

Reactant 5

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

Product 1

HCID 58966940HCID 58966940, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 21959178Acetonitrile pyridineSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-565ff666eb6942fca9f8695a9a6b90b7
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Linked notes

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