Sodium Carbonate → HCID 46941129, compound

HRID 2409582Notes

Reaction equation

HRID 2409582 reaction equation
I[C:2]1[N:9]2[C:5]([S:6][C:7]([C:10]3[CH:11]=[C:12]([N:16]([CH3:18])[CH3:17])[CH:13]=[CH:14][CH:15]=3)=[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+]>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>[CH3:17][N:16]([CH3:18])[C:12]1[CH:11]=[C:10]([C:7]2[S:6][C:5]3=[N:4][CH:3]=[C:2]([C:27]4[CH:28]=[C:29]([C:34]([F:37])([F:36])[F:35])[C:30]([NH2:33])=[N:31][CH:32]=4)[N:9]3[N:8]=2)[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 468641035-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amineHCID 66717075HCID 66717075, compound

Product 1

HCID 46941129HCID 46941129, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
110 °C

Procedure

A mixture of [3-(5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-phenyl]-dimethyl-amine (0.084 g, 0.226 mmol, 1 eq), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (0.098 g, 0.339 mmol, 1.5 eq), 2M aq Na2CO3 (1 mL) and PdCl2(PPh3)2 (0.032 g, 0.045 mmol, 0.2 eq) was heated at 110° C. for 24 h. The solvent was removed in vacuo and the residue was redissolved in DCM/water (150 mL) and extracted 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 (15 mg, 16%) as a yellow solid. HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=5.97 min, [M+H]+ m/z 405.1; 1H NMR (300 MHz, DMSO) δ 8.86 (d, J=1.8 Hz, 1H), 8.45 (d, J=2.0 Hz, 1H), 7.80 (s, 1H), 7.40 (t, J=8.1 Hz, 1H), 7.20 (m, 2H), 6.99 (dd, J=9.1, 2.0 Hz, 1H), 6.75 (s, 2H), 3.00 (s, 6H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was redissolved in DCM/water (150 mL)
  3. extractionextracted with DCM (2×80 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated from MeOH
  8. filtrationfiltered off
  9. customThe solid was purified by column chromatography (0-5% MeOH in DCM)

Sources & evidence

ORD record
ord-5a7ac5e4c1dd401e967cff5a43a22ee4
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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