Ethyl Acetate → HCID 86621265, compound

HRID 605729Notes

Reaction equation

HRID 605729 reaction equation
CC(C1C=C(C(C)C)C=C(C(C)C)C=1S(O[CH:20]([C:22]1([OH:45])[CH2:25][N:24]([C:26]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[C:29]=2[NH:36][C:37]2[CH:42]=[CH:41][C:40]([I:43])=[CH:39][C:38]=2[F:44])=[O:27])[CH2:23]1)[CH3:21])(=O)=O)C.[H-].[Na+].C(OCC)(=O)C>O1CCCC1>[F:35][C:30]1[C:31]([F:34])=[CH:32][CH:33]=[C:28]([C:26]([N:24]2[CH2:25][C:22]3([O:45][CH:20]3[CH3:21])[CH2:23]2)=[O:27])[C:29]=1[NH:36][C:37]1[CH:42]=[CH:41][C:40]([I:43])=[CH:39][C:38]=1[F:44]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 86621264HCID 86621264, compound

Product 1

HCID 86621265HCID 86621265, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-[1-({3,4-Difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-hydroxyazetidin-3-yl]ethyl 2,4,6-tris(1-methylethyl)benzenesulfonate (194 mg, 0.256 mmol) was dissolved in tetrahydrofuran (2 mL) and was cooled to 0° C. Sodium hydride (60 wt % dispersion in oil; 31 mg, 0.775 mmol) was added and the mixture was stirred at 0° C. for 15 minutes. The mixture was quenched with saturated sodium bicarbonate solution and partitioned with ethyl acetate. The aqueous portion was extracted with ethyl acetate. The combined organic portion was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Column chromatography (silica gel, 50% ethyl acetate in hexanes) gave 2,3-difluoro-N-(2-fluoro-4-iodophenyl)-6-[(2-methyl-1-oxa-5-azaspiro[2.3]hex-5-yl)carbonyl]aniline (120 mg, 0.253 mmol, 99% yield): MS (EI) for C18H14F3IN2O2: 475 (MH+).

Workup

  1. customThe mixture was quenched with saturated sodium bicarbonate solution
  2. custompartitioned with ethyl acetate
  3. extractionThe aqueous portion was extracted with ethyl acetate
  4. washThe combined organic portion was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4317580f79f24aadb8c11dc967812412
Source dataset
uspto-grants-2011_03
Patent number
US07915250B2

Reaction notes

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