Sodium Carbonate → HCID 66716941, compound

HRID 2409571Notes

Reaction equation

HRID 2409571 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.[CH2:11]([N:13]1[CH:17]=[C:16](B(O)O)[CH:15]=[N:14]1)[CH3:12].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>[CH2:11]([N:13]1[CH:17]=[C:16]([C:2]2[S:6][C:5]3=[N:7][CH:8]=[C:9]([I:10])[N:4]3[N:3]=2)[CH:15]=[N:14]1)[CH3:12]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 114463761-Ethylpyrazole-4-boronic acidHCID 662215402-Bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 66716941HCID 66716941, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (0.18 g, 0.546 mmol, 1 eq), 1-ethyl-1H-pyrazole-4-boronic acid, pinacol ester (0.145 g, 0.655 mmol, 1.2 eq), Pd(PPh3)2Cl2 (0.077 g, 0.109 mmol, 0.2 eq) and 2M aq Na2CO3 (1 mL) in dioxane (3 mL) was refluxed for 2 h. The solvent was evaporated and the residue was treated with water. The suspension was filtered off (avoid taking the heavier reddish solid) and washed with water. The solid (110 mg) was used in the next step of the synthesis with no further treatment. HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=3.98 min, [M+H]+ m/z 345.9.

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe solvent was evaporated
  3. additionthe residue was treated with water
  4. filtrationThe suspension was filtered off (
  5. washwashed with water
  6. customThe solid (110 mg) was used in the next step of the synthesis with no further treatment
  7. customHPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.)

Sources & evidence

ORD record
ord-6236b6359daa42398720506c0c93b709
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

Loading…