Sodium Carbonate → HCID 25234045, compound

HRID 508343Notes

Reaction equation

HRID 508343 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-594fab1fa9454e9ba40dc6aa27add5c8
Source dataset
uspto-grants-2015_08
Patent number
US09095590B2

Reaction notes

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