Sodium Carbonate → HCID 19046235, compound

HRID 1781301Notes

Reaction equation

HRID 1781301 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]2[CH2:11][O:10][C:9]([C:12]3[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=3[F:19])=[N:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1.CO.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>[F:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([F:18])[C:12]=1[C:9]1[O:10][CH2:11][CH:7]([C:5]2[S:6][C:2]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:3][CH:4]=2)[N:8]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 19046234HCID 19046234, compound

Product 1

HCID 19046235HCID 19046235, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 100 mg (0.3 mmol) of the product of Step D of Example 2 in 0.6 mL toluene was added successively 10.4 mg (0.009 mmol) of Pd (PPh3)4, 0.3 mL of 2.0 m sodium carbonate, and 44 mg (0.36 mmol) of phenylboronic acid in 0.15 mL of methanol. The mixture was stirred at 80° C. for 2 h. It was cooled and partitioned between 25 mL of 2.0 m sodium carbonate containing 2.5 mL of ammonium hydroxide solution and 25 mL of methylene chloride. The methylene chloride layer was washed with brine, dried (MgSO4), and concentrated. The residue was passed through a silica gel flash column eluting with ethyl acetate: hexanes (1:4) to give 85 mg of an oil. 1H-NMR (CDCl3) δ6.90-7.20 (m, 10H), 5.70 (dd,1H), 4.80 (t, 1H), 4.45 (t, 1H).

Workup

  1. temperatureIt was cooled
  2. custompartitioned between 25 mL of 2.0 m sodium carbonate containing 2.5 mL of ammonium hydroxide solution and 25 mL of methylene chloride
  3. washThe methylene chloride layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washeluting with ethyl acetate: hexanes (1:4)

Sources & evidence

ORD record
ord-f7ff2b7c98a8486da666ddbb8f451938
Source dataset
uspto-grants-1997_05
Patent number
US05633271

Reaction notes

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