Sodium Carbonate → HCID 25234045, compound

HRID 2360028Notes

Reaction equation

HRID 2360028 reaction equation
I[C:2]1[CH:3]=[C:4]([N:11]2[CH:16]=[CH:15][C:14](=[O:17])[NH:13][C:12]2=[O:18])[CH:5]=[C:6]([I:10])[C:7]=1[O:8][CH3:9].Br[C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[CH:26]=[C:25]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[CH:24]=[CH:23]2.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[O:18]=[C:12]1[NH:13][C:14](=[O:17])[CH:15]=[CH:16][N:11]1[C:4]1[CH:5]=[C:6]([I:10])[C:7]([O:8][CH3:9])=[C:2]([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[CH:26]=[C:25]([NH:30][S:31]([CH3:34])(=[O:32])=[O:33])[CH:24]=[CH:23]3)[CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 49758834N-(6-Bromonaphthalen-2-yl)methanesulfonamideHCID 57419465HCID 57419465, compound

Product 1

HCID 25234045HCID 25234045, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of the product from Part B 1-(3,5-diiodo-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione (118 mg, 0.25 mmol), the product from Example 4A, Part B (87 mg, 0.25 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride CH2Cl2 complex (10.21 mg, 0.013 mmol) and sodium carbonate (0.250 ml, 0.25 mmol) in toluene (1.0 ml) and ethanol (1.0 ml) was sparged with nitrogen for 5 min and microwaved at 100° C. for 30 min. The mixture was cooled and partitioned with ethyl acetate and 1M HCl. The organic layer was washed with saturated sodium bicarbonate, brine, dried with sodium sulfate, filtered and evaporated. The residue was chromatographed on silica eluting with ethyl acetate/hexane (2:3 to 4:1) to give the title compound (16 mg, 11%). 1H NMR (300 MHz, DMSO-D6) δ ppm 3.08 (s, 3H) 3.35 (s, 3H) 5.67 (d, J=8.09 Hz, 1H) 7.42 (dd, J=8.82, 2.21 Hz, 1H) 7.59 (d, J=2.57 Hz, 1H) 7.73 (m, 2H) 7.81 (d, J=8.09 Hz, 1H) 7.95 (m, 3H) 8.09 (s, 1H) 10.06 (s, 1H) 11.47 (s, 1H). MS (ESI−) m/z 562 (M−H)+.

Workup

  1. custommicrowaved at 100° C. for 30 min
  2. temperatureThe mixture was cooled
  3. custompartitioned with ethyl acetate and 1M HCl
  4. washThe organic layer was washed with saturated sodium bicarbonate, brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed on silica eluting with ethyl acetate/hexane (2:3 to 4:1)

Sources & evidence

ORD record
ord-aa3652c083e64ff88795c7b1ae9e8a72
Source dataset
uspto-grants-2014_04
Patent number
US08685991B2

Reaction notes

Loading…