Sodium Carbonate → HCID 89783120, compound

HRID 877441Notes

Reaction equation

HRID 877441 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[N:11]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:10]=[C:9]([C:18]([F:21])([F:20])[F:19])[CH:8]=2)=[CH:4][CH:3]=1.[CH3:22][S:23]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)(=[O:25])=[O:24].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.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>[CH3:22][S:23]([C:26]1[CH:31]=[C:30]([C:2]2[S:6][C:5]([C:7]3[N:11]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:10]=[C:9]([C:18]([F:21])([F:20])[F:19])[CH:8]=3)=[CH:4][CH:3]=2)[CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 89793114HCID 89793114, compound

Product 1

HCID 89783120HCID 89783120, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A stirred solution of compound 15 (1.5 g, 3.9 mmol) and 3-(methylsulfonyl)phenylboronic acid (1.2 g, 5.8 mmol) in DMF (10 mL) was degassed with argon. Tetrakis(triphenylphosphine)palladium(0) (450 mg, 0.3 mmol) was added and the reaction degassed for 30 min. Sodium carbonate (1.03 g, 9.0 mmol) was added to the reaction mixture, the reaction was degassed with argon for 30 min and heated to 90° C. for 3 h. Solvent was removed and the reaction mixture diluted with water (30 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with saturated brine, dried over sodium sulphate and concentrated. The crude reaction mixture was purified by column chromatography using 30% ethyl acetate in hexane to afford 16 (1.2 g, 67%). LCMS: 459.20 (M+1)+; 1H NMR (DMSO-d6, 400 MHz) δ 8.13 (s, 1H), 8.05 (d, 1H, J=7.6 Hz), 7.91 (d, 1H, J=7.6 Hz), 7.82 (d, 1H, J=4 Hz), 7.75 (t, 2H, J=7.6 Hz) 7.20 (s, 1H), 5.40 (s, 2H), 4.01-4.23 (m, 2H), 3.32 (s, 3H), 1.1-1.25 (m, 3H).

Workup

  1. customthe reaction degassed for 30 min
  2. customthe reaction was degassed with argon for 30 min
  3. customSolvent was removed
  4. additionthe reaction mixture diluted with water (30 mL)
  5. extractionextracted with ethyl acetate (50 mL×3)
  6. washThe combined organic layers were washed with saturated brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated
  9. customThe crude reaction mixture
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-e0efb2984a3d408dbe37b98e1d84758c
Source dataset
uspto-grants-2015_03
Patent number
US08987318B2

Reaction notes

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