Water → HCID 57898991, compound

HRID 911048Notes

Reaction equation

HRID 911048 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1.[CH3:16][C:17]1[N:18]=[C:19]([NH2:22])[S:20][CH:21]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[F:8][C:7]1[C:2]([NH:22][C:19]2[S:20][CH:21]=[C:17]([CH3:16])[N:18]=2)=[N:3][CH:4]=[CH:5][C:6]=1[S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 86634766HCID 86634766, compound

Product 1

HCID 57898991HCID 57898991, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Degassed toluene (10 mL) was added to a mixture of 2-chloro-3-fluoro-4-(phenylthio)pyridine (0.500 g, 2.09 mmol), 4-methylthiazol-2-amine (0.238 g, 2.09 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.0955 g, 0.104 mmol) and potassium phosphate (0.487 g, 2.29 mmol), and then degassed water (3 mL) was added. The reaction was stirred overnight at 90° C., then partitioned between ethyl acetate and water, washed with brine, dried, and concentrated. The crude material was purified by MPLC (Biotage), eluting with 3:1 hexane:ethyl acetate to afford the desired product (0.364 g, 55.0% yield) as white crystals. 1H NMR (d6-DMSO) δ 2.24 (s, 3H), 6.21 (t, 1H), 6.56 (s, 1H), 7.52-7.61 (m, 5H), 7.93 (d, 1H), 11.35 (bs, 1H).

Workup

  1. customDegassed toluene (10 mL)
  2. custompartitioned between ethyl acetate and water
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe crude material was purified by MPLC (Biotage)
  7. washeluting with 3:1 hexane

Sources & evidence

ORD record
ord-3104c449a8144d7f81b4bd468b8f62f7
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

Loading…