Sodium Carbonate → HCID 46941214, compound

HRID 2409596Notes

Reaction equation

HRID 2409596 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[C:4]([NH2:18])=[N:5][CH:6]=[C:7]([C:9]2[S:13][C:12]3=[N:14][CH:15]=[C:16](I)[N:11]3[N:10]=2)[CH:8]=1.[CH3:21][S:22]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)(=[O:24])=[O:23].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([C:16]2[N:11]3[C:12]([S:13][C:9]([C:7]4[CH:8]=[C:3]([C:2]([F:20])([F:19])[F:1])[C:4]([NH2:18])=[N:5][CH:6]=4)=[N:10]3)=[N:14][CH:15]=2)=[CH:27][CH:26]=1)(=[O:24])=[O:23]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 66716934HCID 66716934, compound

Product 1

HCID 46941214HCID 46941214, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

3-(trifluoromethyl)-5-(5-iodoimidazo[2,1-b][1,3,4]thiadiazol-2-yl)pyridin-2-amine (0.100 g, 0.243 mmol, 1 eq) was dissolved in dioxane (1.5 mL), then 4-(methylsulfonyl)phenylboronic acid (0.078 g, 0.389 mmol, 1.6 eq) was added followed by 2M aq. Na2CO3 (0.5 mL, 4 eq). The suspension was degassed (N2, 15 min) and equipped with an argon balloon. Pd(Ph3P)2Cl2 (0.043 g, 0.061 mmol, 0.25 eq) was quickly added, and the reaction flask was placed in a pre-heated bath (115° C.). After stirring at reflux temperature for 3 h the mixture was cooled to RT and concentrated. The residue was taken up in water, and the solid obtained was filtered off, washed with Et2O and dried. The crude product was suspended in CH3CN at 50° C., filtered off and dried in vacuo to afford the desired product (0.061 g, 57%). HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=4.04 min, [M+H]+ m/z 440.0; 1H-NMR (DMSO-d6+TFA): δ=8.88 (1H, s), 8.36 (2H, d, J=8.4 Hz), 8.28 (1H, s), 8.17 (1H, s), 8.06 (2H, d, J=8.4 Hz), 3.24 (3H, s) ppm.

Workup

  1. customThe suspension was degassed (N2, 15 min)
  2. customequipped with an argon balloon
  3. customthe reaction flask was placed in a pre-heated bath
  4. custom(115° C.)
  5. temperatureat reflux temperature for 3 h the mixture
  6. concentrationconcentrated
  7. customthe solid obtained
  8. filtrationwas filtered off
  9. washwashed with Et2O
  10. customdried
  11. customwas suspended in CH3CN at 50° C.
  12. filtrationfiltered off
  13. customdried in vacuo

Sources & evidence

ORD record
ord-55f1eb1ab7834ed1aadee498f4723b3d
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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