3-Iodobenzoic acid → HCID 58181859, compound

HRID 237313Notes

Reaction equation

HRID 237313 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[F:11][C:12]1([F:18])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[F:11][C:12]1([F:18])[CH2:17][CH2:16][N:15]([C:5]([C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=2)=[O:7])[CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 120603-Iodobenzoic acidHCID 81531DiisopropylethylamineHCID 27583524,4-DifluoropiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 58181859HCID 58181859, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-iodobenzoic acid 1 (482 mg, 1.94 mmol) in DMF (6 mL) was added 4,4-difluoropiperidine 2 (259 mg, 2.14 mmol), HATU (886 mg, 2.33 mmol) and diisopropylethylamine (750 mg, 5.81 mmol). The reaction mixture was stirred at room temperature for 1.5 hours. Ethyl acetate (100 mL) was added and the organic layer was washed with 1 N sodium hydroxide solution, 1 N hydrochloric acid, water and brine. The organic layer was dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure. The crude product was purified by flash column chromatography to afford the desired 4,4-difluoro-1-[(3-iodophenyl)carbonyl]piperidine compound 77-1 (362 mg, 1.03 mmol).

Workup

  1. washthe organic layer was washed with 1 N sodium hydroxide solution, 1 N hydrochloric acid, water and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customThe organic solvent was evaporated under reduced pressure
  4. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-2c1140631b9f42a08c15130dd191c2c0
Source dataset
uspto-grants-2014_02
Patent number
US08642582B2

Reaction notes

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