Pyrrolidine → HCID 67324968, compound

HRID 1028988Notes

Reaction equation

HRID 1028988 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([F:12])=[CH:7][C:3]=1[C:4]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:6]

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534305262-Bromo-5-fluoro-3-methylbenzoic acid

Product 1

HCID 67324968HCID 67324968, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-5-fluoro-3-methylbenzoic acid (140 mg, 0.60 mmol), pyrrolidine (99 μL, 1.20 mmol) and Hunig's base (210 μL, 1.20 mmol) in DMF (2 mL) at RT was added HATU (457 mg, 1.20 mmol) and the reaction stirred at this temp overnight. The reaction was quenched with water and the aqueous layer was extracted with EtOAc. The organic layer was then washed with water and brine (3× ea.), dried over Na2SO4 and concentrated in vacuo. The crude material was purified by column chromatography (0-60% Hex/EtOAC) to yield (2-bromo-5-fluoro-3-methylphenyl)(pyrrolidin-1-yl)methanone as a clear oil.

Workup

  1. customThe reaction was quenched with water
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe organic layer was then washed with water and brine (3× ea.)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by column chromatography (0-60% Hex/EtOAC)

Sources & evidence

ORD record
ord-5fa10cfe6fd94a7eb38b7b2425fc714c
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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