Sodium Carbonate → HCID 66690597, compound

HRID 2409592Notes

Reaction equation

HRID 2409592 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[S:12][C:11]2=[N:13][CH:14]=[C:15]([I:16])[N:10]2[N:9]=1.[NH2:17][C:18]1[CH:19]=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:21]=[N:22][C:23]=1[O:24][CH3:25]>O1CCOCC1>[I:16][C:15]1[N:10]2[C:11]([S:12][C:8]([C:20]3[CH:19]=[C:18]([NH2:17])[C:23]([O:24][CH3:25])=[N:22][CH:21]=3)=[N:9]2)=[N:13][CH:14]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 595579202-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amineHCID 662215402-Bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 66690597HCID 66690597, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Dioxane (5 mL) and 2M aq Na2CO3 (1.5 mL) were added to 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (200 mg) and (5-amino-6-methoxypyridin-3-yl)boronic acid pinacol ester (200 mg), and the suspension was degassed under vacuum and filled with argon (3×). PdCl2(PPh3)2 (90 mg) was quickly added, and the reaction mixture was stirred at reflux for 2 h. Water was added, and a precipitate formed that was filtered off and washed with water followed by ether and ether/MeOH 10:1 and dried to give the desired product (150 mg) that was used without further purification in the subsequent step. HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=4.12 min, [M+H]+ m/z 373.9.

Workup

  1. customthe suspension was degassed under vacuum
  2. additionfilled with argon (3×)
  3. additionPdCl2(PPh3)2 (90 mg) was quickly added
  4. temperatureat reflux for 2 h
  5. additionWater was added
  6. customa precipitate formed
  7. filtrationthat was filtered off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-d5f8c5308a704338832ad2f29ca7d967
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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