tert-Butanol → HCID 58734253, compound

HRID 2080494Notes

Reaction equation

HRID 2080494 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:20]([CH2:23]C)CC)C.[Br:25][C:26]1[C:27]([CH:35]([S:44]([C:47]2[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49][CH:48]=2)(=[O:46])=[O:45])[C:36]2[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=2[F:43])=[CH:28][C:29](C(O)=O)=[N:30][CH:31]=1.C(OCC)(=[O:56])C.[C:60]([OH:64])([CH3:63])([CH3:62])[CH3:61]>C1(C)C=CC=CC=1.CCCCCC>[C:60]([O:64][C:23](=[O:56])[NH:20][C:29]1[CH:28]=[C:27]([CH:35]([S:44]([C:47]2[CH:48]=[CH:49][C:50]([Cl:53])=[CH:51][CH:52]=2)(=[O:45])=[O:46])[C:36]2[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=2[F:43])[C:26]([Br:25])=[CH:31][N:30]=1)([CH3:63])([CH3:62])[CH3:61]

Participants

8

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 23114610HCID 23114610, compound

Product 1

HCID 58734253HCID 58734253, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

Under an argon atmosphere, diphenylphosphoryl azide (131 μl, 0.613 mmol) and triethylamine (122 μl, 0.875 mmol) were added to a solution of 5-bromo-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]picolinic acid (220 mg, 0.438 mmol) in a mixture of t-butanol (5 ml) and toluene (5 ml). The reaction mixture was stirred for 14 hours under heating and refluxing. After cooling, ethyl acetate was added to the residue. The resulting mixture was washed sequentially with a saturated aqueous solution of sodium bicarbonate and brine. The organic layer thus obtained was dried over magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=4:1 eluate was concentrated under reduced pressure to give the title compound (128 mg, 0.223 mmol, 51%) as a white powder.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing
  3. temperatureAfter cooling
  4. washThe resulting mixture was washed sequentially with a saturated aqueous solution of sodium bicarbonate and brine
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained
  9. concentrationethyl acetate=4:1 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ae048d4923f041f1b50c2cdf303e8daa
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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