Potassium Carbonate → HCID 59232734, compound

HRID 2426985Notes

Reaction equation

HRID 2426985 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9]([CH3:19])([CH3:18])[C:10]([NH:12][C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[O:11])=[CH:4][CH:3]=1.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.C([O-])([O-])=O.[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.CN(C=O)C>[CH3:18][C:9]([CH3:19])([CH:8]([C:5]1[CH:6]=[CH:7][C:2]([C:31]2[CH:32]=[CH:33][C:28]([O:27][CH3:26])=[CH:29][CH:30]=2)=[CH:3][CH:4]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:10]([NH:12][C:13]1[S:14][CH:15]=[CH:16][N:17]=1)=[O:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 59232719HCID 59232719, compound

Product 1

HCID 59232734HCID 59232734, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

An Emry™ process vial was charged with 3-(4-bromo-phenyl)-2,2-dimethyl-3-phenyl-N-thiazol-2-yl-propionamide (70 mg, 0.168 mmol) and 4-methoxy-phenylboronic acid (77 mg, 0.50 mmol), tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol), 2.0 mL of 2M K2CO3, and 1.5 mL of DMF. The reaction mixture was degassed by bubbling nitrogen through for 15 min, then sealed and exposed to microwave irradiation for 30 min at 150° C. The reaction mixture was cooled, filtered, and diluted with ethyl acetate. The organic solution was washed, dried and concentrated. The crude product was purified by preparative HPLC to give the title compound of Example 374 as a white solid (30 mg, 40%). LC/MS (m/z) 444.37 [(M+H)+]; HPLC Rt: 3.770 min. 1H NMR (400 MHz, MeOD) δ ppm 7.34-7.54 (9H, m) 7.23 (2H, t, J=7.38 Hz) 7.16 (1H, t, J=7.12 Hz) 7.02 (1H, d, J=3.56 Hz) 6.93 (2H, d, J=8.65 Hz) 4.63 (1H, s) 3.78 (3H, s) 1.40 (6H, s).

Workup

  1. customThe reaction mixture was degassed
  2. customby bubbling nitrogen through for 15 min
  3. customsealed
  4. customirradiation for 30 min at 150° C
  5. temperatureThe reaction mixture was cooled
  6. filtrationfiltered
  7. additiondiluted with ethyl acetate
  8. washThe organic solution was washed
  9. customdried
  10. concentrationconcentrated
  11. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-0a8f26f33cef48798a6acc62781ee60c
Source dataset
uspto-grants-2011_06
Patent number
US07968577B2

Reaction notes

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