Sodium Carbonate → HCID 67298601, compound

HRID 1009255Notes

Reaction equation

HRID 1009255 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:12][C@H:13]([C:18]([NH:20][C:21]2([C:24]#[N:25])[CH2:23][CH2:22]2)=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])[CH:9]([F:11])[F:10])=[CH:4][CH:3]=1.[CH3:26][S:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.C([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CN(C=O)C>[C:24]([C:21]1([NH:20][C:18](=[O:19])[C@H:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[NH:12][C@@H:8]([C:5]2[CH:6]=[CH:7][C:2]([C:31]3[CH:32]=[CH:33][C:28]([S:27][CH3:26])=[CH:29][CH:30]=3)=[CH:3][CH:4]=2)[CH:9]([F:11])[F:10])[CH2:23][CH2:22]1)#[N:25]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 27339594-(Methylthio)phenylboronic acidHCID 67298080HCID 67298080, compound

Product 1

HCID 67298601HCID 67298601, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A stream of nitrogen was passed through a suspension of the aryl bromide from Step 5 (65 mg), 4-(methylthio)phenylboronic acid (40 mg), 2 M Na2CO3 (0.22 mL) and DMF (1.0 mL) for 5 minutes. PdCl2dppf was then added and the reaction was warmed to 80° C. and stirred under nitrogen for 4 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (20 mL) and poured into a saturated solution of sodium bicarbonate. The ethyl acetate layer was separated and the aqueous further extracted with ethyl acetate (2×15 mL). The combined ethyl acetate extracts were washed with brine and dried with magnesium sulfate. Removal of the solvent left a residue that was purified by chromatography on SiO2 using a gradient of hexanes and ethyl acetate (90:10 to 50:50) to afford the title compound.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe ethyl acetate layer was separated
  3. extractionthe aqueous further extracted with ethyl acetate (2×15 mL)
  4. washThe combined ethyl acetate extracts were washed with brine
  5. dry with materialdried with magnesium sulfate
  6. customRemoval of the solvent
  7. waitleft a residue that
  8. customwas purified by chromatography on SiO2 using a gradient of hexanes and ethyl acetate (90:10 to 50:50)

Sources & evidence

ORD record
ord-3d53d99344774b41a550c369952b482e
Source dataset
uspto-grants-2011_07
Patent number
US07973037B2

Reaction notes

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