Triethylamine → HCID 86710134, compound

HRID 1468302Notes

Reaction equation

HRID 1468302 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([CH:11]([CH3:13])[CH3:12])[N:10]=[C:4]2[CH:3]=1.[Cl:14][S:15](O[Si](C)(C)C)(=[O:17])=[O:16].C(N(CC)CC)C.P(Cl)(Cl)(Cl)=O>ClCCCl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([S:15]([Cl:14])(=[O:17])=[O:16])=[C:9]([CH:11]([CH3:13])[CH3:12])[N:10]=[C:4]2[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 78059Trimethylsilyl chlorosulphateHCID 82388494HCID 82388494, compound

Product 1

HCID 86710134HCID 86710134, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

7-Bromo-2-isopropylimidazo[1,2-a]pyridine (1.00 g, 4.18 mmol) obtained in step 1 of Example 28 was dissolved in 1,2-dichloroethane (10 mL). Under ice-cooled condition, trimethylsilyl chlorosulfonate (1.20 mL, 8.36 mmol) was added, and the mixture was stirred at 90° C. for 3 hours. Under ice-cooled condition, triethylamine (1.17 mL, 8.36 mmol) and phosphoryl chloride (0.779 mL, 8.36 mmol) were added, and the mixture was stirred at 100° C. for 1.5 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in acetonitrile. After adding a sodium hydrogen carbonate aqueous solution, the precipitated solid was collected by filteration to give 7-bromo-2-isopropylimidazo[1,2-a]pyridine-3-sulfonylchloride (1.31 g, yield 93%).

Workup

  1. additionwas added
  2. additionwere added
  3. stirringthe mixture was stirred at 100° C. for 1.5 hours
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in acetonitrile
  6. additionAfter adding a sodium hydrogen carbonate aqueous solution
  7. customthe precipitated solid was collected by filteration

Sources & evidence

ORD record
ord-0012150464644208a979308b18590fec
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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