Sodium Carbonate → HCID 66716902, compound

HRID 2409589Notes

Reaction equation

HRID 2409589 reaction equation
I[C:2]1[N:9]2[C:5]([S:6][C:7]([C:10]3[CH:11]=[C:12]([NH:16][C:17](=[O:19])[CH3:18])[CH:13]=[CH:14][CH:15]=3)=[N:8]2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:28]2[CH:29]=[C:30]([C:35]([F:38])([F:37])[F:36])[C:31]([NH2:34])=[N:32][CH:33]=2)O1.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>[NH2:34][C:31]1[N:32]=[CH:33][C:28]([C:2]2[N:9]3[C:5]([S:6][C:7]([C:10]4[CH:11]=[C:12]([NH:16][C:17](=[O:19])[CH3:18])[CH:13]=[CH:14][CH:15]=4)=[N:8]3)=[N:4][CH:3]=2)=[CH:29][C:30]=1[C:35]([F:38])([F:36])[F:37]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 468641035-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amineHCID 66717031HCID 66717031, compound

Product 1

HCID 66716902HCID 66716902, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of N-[3-(5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-phenyl]-acetamide (0.16 g, 0.416 mmol, 1 eq), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (0.12 g, 0.416 mmol, 1 eq), 2M aq Na2CO3 (0.9 mL) and PdCl2(PPh3)2 (60 mg, 0.083 mmol, 0.2 eq) in dioxane (5 mL) was heated at 110° C. for 90 min. The solvent was removed under reduced pressure and the residue was redissolved in DCM and washed with water. The organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified by flash-chromatography (DCM: MeOH, 5 to 15%) and by HPLC to afford the desired product (7 mg, 4%). HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=4.74 min, [M+H]+ m/z 419.1; 1H NMR (300 MHz, DMSO) δ 10.30 (s, 1H), 8.89 (s, 1H), 8.32 (m, 2H), 7.81 (m, 2H), 7.62 (d, J=7.8 Hz, 1H), 7.54 (t, J=7.9 Hz, 1H), 6.75 (s, 2H), 2.09 (s, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was redissolved in DCM
  3. washwashed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash-chromatography (DCM: MeOH, 5 to 15%) and by HPLC

Sources & evidence

ORD record
ord-5f6743b7abc44c46866b9e907edac91b
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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