Sodium Carbonate → HCID 66717262, compound

HRID 2409580Notes

Reaction equation

HRID 2409580 reaction equation
I[C:2]1[N:9]2[C:5]([S:6][C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:11]=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+]>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.O1CCOCC1>[CH3:19][S:16]([C:12]1[CH:11]=[C:10]([C:7]2[S:6][C:5]3=[N:4][CH:3]=[C:2]([C:28]4[CH:29]=[C:30]([C:35]([F:38])([F:37])[F:36])[C:31]([NH2:34])=[N:32][CH:33]=4)[N:9]3[N:8]=2)[CH:15]=[CH:14][CH:13]=1)(=[O:18])=[O:17]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 468641035-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amineHCID 66717127HCID 66717127, compound

Product 1

HCID 66717262HCID 66717262, compoundYield 20.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-Iodo-2-(3-methanesulfonyl-phenyl)-imidazo[2,1-b][1,3,4]thiadiazole (0.091 g, 0.225 mmol, 1 eq), and 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (0.097 g, 0.337 mmol, 1.5 eq), PdCl2(PPh3)2 (32 mg, 0.045 mmol, 0.2 eq) and 2M Na2CO3 (1 mL) and dioxane (5 mL). The reaction mixture was heated at 110° C. for 24 h. The solvent was evaporated, the residue was redissolved in DCM/water (150 mL) and extacted with DCM (2×80 mL). The organic layer was dried (MgSO4), filtered and evaporated. The residue was triturated from MeOH and filtered off. The solid was purified by column chromatography (0-5% MeOH in DCM) to give the desired product (20 mg, 20%) as a yellow solid. HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=5.25 min, [M+H]+ m/z 440.0; 1H NMR (300 MHz, DMSO) δ 8.90 (d, J=1.8 Hz, 1H), 8.44 (d, J=1.6 Hz, 1H), 8.37 (d, J=2.0 Hz, 1H), 8.33 (d, J=7.9 Hz, 1H), 8.19 (d, J=8.1 Hz, 1H), 7.92 (t, J=7.9 Hz, 1H), 7.84 (s, 1H), 6.74 (s, 2H), 3.32 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was redissolved in DCM/water (150 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was triturated from MeOH
  7. filtrationfiltered off
  8. customThe solid was purified by column chromatography (0-5% MeOH in DCM)

Sources & evidence

ORD record
ord-c6539889bfd842a69f37cc2b73ba7f9c
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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