Sodium Carbonate → HCID 86656712, compound

HRID 451513Notes

Reaction equation

HRID 451513 reaction equation
Br[C:2]1[C:7]2[N:8]=[C:9]([NH:11]C(=O)OC(C)(C)C)[S:10][C:6]=2[CH:5]=[C:4]([CH3:19])[CH:3]=1.[Cl:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][C:26]=1[F:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:20][C:21]1[CH:22]=[C:23]([C:2]2[C:7]3[N:8]=[C:9]([NH2:11])[S:10][C:6]=3[CH:5]=[C:4]([CH3:19])[CH:3]=2)[CH:24]=[CH:25][C:26]=1[F:27]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 86656711HCID 86656711, compound

Product 1

HCID 86656712HCID 86656712, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of tert-butyl 4-bromo-6-methylbenzo[d]thiazol-2-ylcarbamate (0.6 g, 1.75 mmol), 3-chloro-4-fluorophenylboronic acid (0.5 g, 2.62 mmol), palladium(II) acetate (0.08 g, 0.35 mmol), triphenylphosphine (0.3 g, 1.05 mmol) was added degassed dioxane (10 mL) and degassed 1 M aqueous sodium carbonate (5.24 mL, 5.24 mmol). The mixture was heated to 100° C. for 16 hours under argon and then diluted with ethyl acetate, washed with water, brine and concentrated. The residue was redissolved in trifluoroacetic acid (2 mL) and stirred for 15 minutes. The solvent was evaporated, the residue redissolved in dichloromethane, washed with saturated sodium hydrogen carbonate, dried with sodium sulfate and concentrated. The product was purified by column chromatography on silica gel using n-heptane:ethyl acetate (v/v=9:1-4:1) as eluent to yield the title compound as white solid (0.4 g, 80%).

Workup

  1. additionwas added
  2. customdegassed dioxane (10 mL)
  3. washwashed with water, brine
  4. concentrationconcentrated
  5. dissolutionThe residue was redissolved in trifluoroacetic acid (2 mL)
  6. customThe solvent was evaporated
  7. dissolutionthe residue redissolved in dichloromethane
  8. washwashed with saturated sodium hydrogen carbonate
  9. dry with materialdried with sodium sulfate
  10. concentrationconcentrated
  11. customThe product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d35bfe7da7854cc99c861d8ce792850d
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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