Sodium Carbonate → HCID 66717020, compound

HRID 2409578Notes

Reaction equation

HRID 2409578 reaction equation
I[C:2]1[N:9]2[C:5]([S:6][C:7]([C:10]3[CH:11]=[C:12]4[C:16](=[CH:17][CH:18]=3)[NH:15][CH:14]=[CH:13]4)=[N:8]2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[C:29]([C:34]([F:37])([F:36])[F:35])[C:30]([NH2:33])=[N:31][CH:32]=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>[NH:15]1[C:16]2[C:12](=[CH:11][C:10]([C:7]3[S:6][C:5]4=[N:4][CH:3]=[C:2]([C:27]5[CH:28]=[C:29]([C:34]([F:37])([F:36])[F:35])[C:30]([NH2:33])=[N:31][CH:32]=5)[N:9]4[N:8]=3)=[CH:18][CH:17]=2)[CH:13]=[CH:14]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 468641035-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amineHCID 67283603HCID 67283603, compound

Product 1

HCID 66717020HCID 66717020, compoundYield 12.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-(5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-1H-indole (0.091 g, 0.247 mmol, 1 eq), 5-(4,4,5,5-tetramethyl[-1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (0.107 g, 0.371 mmol, 1.5 eq), 2M aq Na2CO3 (1 mL) and PdCl2(PPh3)2 (0.035 g, 0.049 mmol, 0.2 eq) in dioxane (5 mL) was heated at 110° C. for 24 h. The solvent was removed in vacuo, 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 purified by column chromatography (0-10% MeOH in DCM and a second column 0-5% MeOH in DCM) to afford the desired product (12 mg, 12%) as a yellow solid. HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=5.08 min, [M+H]+ m/z 401.0; 1H NMR (300 MHz, DMSO) δ 11.57 (s, 1H), 8.90 (d, J=1.8 Hz, 1H), 8.39 (d, J=2.1 Hz, 1H), 8.20 (d, J=1.6 Hz, 1H), 7.75 (s, 1H), 7.73 (dd, J=9.2, 2.4 Hz, 1H), 7.61 (d, J=8.6 Hz, 1H), 7.52 (m, 1H), 6.73 (s, 2H), 6.64 (s, 1H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionredissolved in DCM/water (150 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (0-10% MeOH in DCM

Sources & evidence

ORD record
ord-cd53aec242eb47e9b10a028ec3722684
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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