Cesium carbonate → HCID 66717075, compound

HRID 2409581Notes

Reaction equation

HRID 2409581 reaction equation
Br[C:2]1[S:6][C:5]2=[N:7][CH:8]=[C:9]([I:10])[N:4]2[N:3]=1.[CH3:11][N:12]([C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)[CH3:13].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[I:10][C:9]1[N:4]2[C:5]([S:6][C:2]([C:18]3[CH:19]=[C:14]([N:12]([CH3:13])[CH3:11])[CH:15]=[CH:16][CH:17]=3)=[N:3]2)=[N:7][CH:8]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27625273-(Dimethylamino)benzeneboronic acid2×HCID 662215402-Bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 66717075HCID 66717075, compoundYield 21.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (0.150 g, 0.455 mmol, 1 eq), 3-(N,N-dimethylamino)phenylboronic acid (0.113 g, 0.682 mmol, 1.5 eq), Cs2CO3 (0.296 g, 0.909 mmol, 2 eq) and Pd(PPh3)4 (0.032 g, 0.027 mmol, 0.06 eq) were dissolved in Dioxane (8 mL) and water (2 mL). The reaction mixture was heated at 95° C. for 24 h. Additional amounts of 3-(N,N-dimethylamino)phenylboronic acid (1.5 eq) and Pd(PPh3)4 (0.06 eq) were added and the reaction mixture was heated at 95° C. for 3 days. The solvent was removed in vacuo, redissolved in DCM/water (150 mL) and extracted with DCM (2×80 mL). The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (20-70% EtOAc in cyclohexane) to afford the desired product (36 mg, 21%) as a yellow solid. HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=4.73 min, [M+H]+ m/z 371.1.

Workup

  1. temperaturethe reaction mixture was heated at 95° C. for 3 days
  2. customThe solvent was removed in vacuo
  3. dissolutionredissolved in DCM/water (150 mL)
  4. extractionextracted with DCM (2×80 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography (20-70% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-7461b7d47a8844fea535952e88e61502
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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