Potassium Phosphate, Tribasic → N-(5-(6-fluoro-3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)pyridin-3-yl)ethanesulfonamide

HRID 1253935Notes

Reaction equation

HRID 1253935 reaction equation
[F:1][C:2]1[C:12](B2OC(C)(C)C(C)(C)O2)=[CH:11][C:5]2[N:6]([CH3:10])[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.Br[C:23]1[CH:24]=[C:25]([NH:29][S:30]([CH2:33][CH3:34])(=[O:32])=[O:31])[CH:26]=[N:27][CH:28]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[C:12]([C:23]2[CH:24]=[C:25]([NH:29][S:30]([CH2:33][CH3:34])(=[O:32])=[O:31])[CH:26]=[N:27][CH:28]=2)=[CH:11][C:5]2[N:6]([CH3:10])[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66788384N-(5-bromopyridin-3-yl)ethanesulfonamideHCID 667979276-fluoro-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2(3H)-one

Product 1

HCID 49802023N-(5-(6-fluoro-3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)pyridin-3-yl)ethanesulfonamide

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

A flask was charged with 6-fluoro-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2(3H)-one (220 mg, 0.751 mmol), N-(5-bromopyridin-3-yl)ethanesulfonamide (133 mg, 0.5 mmol), K3PO4 (212 mg, 1.0 mmol) and Pd(PPh3)4 (28.9 mg, 0.025 mmol). The flask was flushed with N2 and DMF (5 mL) was added. The mixture was stirred under N2 at 100° C. for 1 h. The mixture was cooled to room temperature, diluted with EtOAc (100 mL) and filtered through a pad of celite. The celite pad was washed with EtOAc (100 mL) and the combined organic phase was washed with water (50 mL*2) and brine (50 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica chromatography eluting with a 0 to 80% EtOAc-heptane gradient to give N-(5-(6-fluoro-3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)pyridin-3-yl)ethanesulfonamide. 1H NMR (400 MHz, DMSO-d6) d ppm 1.23 (t, J=7.33 Hz, 3H) 3.21 (q, J=7.33 Hz, 2H) 3.38 (s, 3H) 7.53 (d, J=6.57 Hz, 1H) 7.58 (d, J=10.11 Hz, 1H) 7.79 (q, J=1.85 Hz, 1H) 8.47 (d, J=2.27 Hz, 1H) 8.49 (t, J=1.52 Hz, 1H) 10.20 (s, 1H). HRMS: (ESI) m/z 352.0769 [(M+H)+Calcd for C15H15FN3O4S 352.07618].

Workup

  1. customThe flask was flushed with N2 and DMF (5 mL)
  2. additionwas added
  3. temperatureThe mixture was cooled to room temperature
  4. additiondiluted with EtOAc (100 mL)
  5. filtrationfiltered through a pad of celite
  6. washThe celite pad was washed with EtOAc (100 mL)
  7. washthe combined organic phase was washed with water (50 mL*2) and brine (50 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica chromatography
  11. washeluting with a 0 to 80% EtOAc-heptane gradient

Sources & evidence

ORD record
ord-30cef995c710441da47cee8a0790cbbe
Source dataset
uspto-grants-2013_06
Patent number
US08455522B2

Reaction notes

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