Potassium Carbonate → HCID 46886349, compound

HRID 910771Notes

Reaction equation

HRID 910771 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:16]3[CH2:15][CH2:14][CH2:13][CH:12]([OH:17])[C:11]=3[C:10](=[O:18])[C:9]([C:19]([OH:21])=[O:20])=[CH:8]2)=[CH:4][CH:3]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[CH3:58][O:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CS(C)=O>[OH:17][CH:12]1[CH2:13][CH2:14][CH2:15][C:16]2[N:7]([CH2:6][C:5]3[CH:22]=[CH:23][C:2]([C:61]4[CH:62]=[CH:63][CH:64]=[CH:65][C:60]=4[O:59][CH3:58])=[CH:3][CH:4]=3)[CH:8]=[C:9]([C:19]([OH:21])=[O:20])[C:10](=[O:18])[C:11]1=2

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 59627846HCID 59627846, compound

Product 1

HCID 46886349HCID 46886349, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A 2-dram screw-cap vial was charged with the above carboxylic acid (51 mg, 0.13 mmol), X-Phos (7.7 mg, 0.016 mmol), 2-methoxyphenyl boronic acid (32 mg, 0.21 mmol), and dimethyl sulfoxide (1 mL). The mixture was stirred vigorously and potassium carbonate (46 mg, 0.33 mmol) in 0.2 mL of water was added along with palladium (II) acetate (3.6 mg, 0.0053 mmol). The mixture was heated at 80° C. for 90 minutes, cooled to ambient temperature and filtered. The mixture was purified via preparative reverse phase HPLC to provide the titled compound: 1H-NMR (500 MHz, d6-DMSO) δ 8.93 (1H, s), 7.51 (2H, d, J=10.4 Hz), 7.35 (1H, t, J=7.4 Hz), 7.28 (1H, d, J=7.4 Hz), 7.17 (2H, d, J=8.9 Hz), 7.11 (1H, d, J=7.4 Hz), 7.02 (1H, t, J=7.4 Hz), 5.59 (1H, d, J=16.3 Hz), 5.52 (1H, d, J=16.3 Hz), 4.89 (1H, br s), 3.75 (3H, s), 2.83 (1H, m), 1.87 (1H, m), 1.79-1.73 (2H, m), 1.48 (1H, m) ppm; high resolution mass spectrum (ES+) m/z 406.1631 [(M+H)+; calculated for C24H24NO5: 406.1649].

Workup

  1. customA 2-dram screw-cap vial
  2. temperaturecooled to ambient temperature
  3. filtrationfiltered
  4. customThe mixture was purified via preparative reverse phase HPLC

Sources & evidence

ORD record
ord-a90a9f1aa7484c14b0d82c9ee8817954
Source dataset
uspto-grants-2011_09
Patent number
US08022215B2

Reaction notes

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