Water → HCID 71105640, compound

HRID 927624Notes

Reaction equation

HRID 927624 reaction equation
[C:1]([C@@H:4]([NH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[C:14](Cl)[N:13]=1)=[O:11])[CH2:5][CH:6]([CH3:8])[CH3:7])(=[O:3])[NH2:2].[F:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C>[C:1]([C@@H:4]([NH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[C:14]([O:27][C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)[N:13]=1)=[O:11])[CH2:5][CH:6]([CH3:8])[CH3:7])(=[O:3])[NH2:2]

Participants

6

Reactant 4

HCID 962WaterHCID 97324-FluorophenolHCID 10340Sodium CarbonateHCID 86674776HCID 86674776, compound

Product 1

HCID 71105640HCID 71105640, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

5-Bromo-6-chloro-pyridine-2-carboxylic acid ((S)-1-carbamoyl-3-methyl-butyl)-amide (50 mg, 143 μmol) was dissolved in DMF (0.5 mL) to give a colorless solution. 4-Fluorophenol (19.3 mg, 172 μmol) and sodium carbonate (45.6 mg, 430 μmol) were added successively to give a yellow solution. The reaction mixture was stirred at 120° C. over the weekend, cooled to ambient temperature and poured into 40 mL water. The mixture was extracted with isopropyl acetate (2×40 mL), organic phases were combined, dried with Na2SO4 and concentrated in vacuo. The residue was purified by preparative TLC (silica gel, 2.0 mm, isopropyl acetate) to give the title compound (23 mg, 38%) as colorless oil, MS (ESI): m/e=421.9 [M−H]−.

Workup

  1. customto give a colorless solution
  2. customto give a yellow solution
  3. temperaturecooled to ambient temperature
  4. extractionThe mixture was extracted with isopropyl acetate (2×40 mL), organic phases
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative TLC (silica gel, 2.0 mm, isopropyl acetate)

Sources & evidence

ORD record
ord-36413ced708142faab8319c6e487568c
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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