Sodium Carbonate → HCID 18439657, compound

HRID 457580Notes

Reaction equation

HRID 457580 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[O:12][C:11]([NH:13][C:14]3[CH:19]=[C:18]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH:17]=[CH:16][C:15]=3[O:25][CH3:26])=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:27]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)#[N:28].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[CH2:23]([S:20]([C:18]1[CH:17]=[CH:16][C:15]([O:25][CH3:26])=[C:14]([NH:13][C:11]2[O:12][C:8]([C:4]3[CH:3]=[C:2]([C:32]4[CH:33]=[CH:34][C:29]([C:27]#[N:28])=[CH:30][CH:31]=4)[CH:7]=[CH:6][CH:5]=3)=[CH:9][N:10]=2)[CH:19]=1)(=[O:22])=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 11487418HCID 11487418, compound

Product 1

HCID 18439657HCID 18439657, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the title compound of Example 100 (250 mg, 0.57 mmol), 4-cyanophenyl boronic acid (108 mg, 0.74 mmol), 2M aqueous sodium carbonate solution (0.5 mL, 1.0 mmol), and (bistriphenylphosphine)palladium(II) chloride (50 mg, 0.071 mmol) was suspended in DMF (2 mL) and stirred at 100° C. After 20 min, the reaction was determined to be complete by TLC analysis. After cooling to RT, the DMF was evaporated under reduced pressure. The crude product was partitioned between dichloromethane (50 mL) and water (50 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (1:1) to afford the title compound (152 mg, 58%) as a solid white powder. 1H NMR (400 MHz, d6-DMSO): δ 9.82 (s, 1H), 8.81 (d, J=2.2, 1H), 7.95–8.05 (m, 5H), 7.68–7.74 (m, 3H), 7.63 (d, J=7.8, 1H), 7.53 (dd, J1=2.2, J2=8.7, 1H), 7.31 (d, J=8.5, 1H), 4.01 (s, 3H), 3.24 (q, J=7.3, 2H), 1.14 (t, J=7.3, 3H). MS (ES+, m/z)=459 (m+H)+.

Workup

  1. temperatureAfter cooling to RT
  2. customthe DMF was evaporated under reduced pressure
  3. customThe crude product was partitioned between dichloromethane (50 mL) and water (50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-63cbf0c15a664a08b002b49eaaf51dfd
Source dataset
uspto-grants-2007_03
Patent number
US07189712B2

Reaction notes

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