Bicarbonate Ion → Fluoromidine

HRID 437399

Reaction equation

HRID 437399 reaction equation
CS(O[N:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([Cl:15])[CH:13]=2)[N:8]=[C:7]1[C:16]([F:19])([F:18])[F:17])(=O)=O.[I-].[Na+].CCOCC.C(=O)(O)[O-]>CC(C)=O>[Cl:15][C:12]1[CH:13]=[C:14]2[NH:6][C:7]([C:16]([F:17])([F:18])[F:19])=[N:8][C:9]2=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 3283Diethyl EtherHCID 5238Sodium IodideHCID 203599241-(METHYLSULFONYLOXY)-6-CHLORO-2-(TRIFLUOROMETHYL)-1H-IMIDAZO(4,5-b)PYRIDINE

Product 1

HCID 911208FluoromidineYield 73%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

1-(Methylsulfonyloxy)-6-chloro-2-(trifluoromethyl)-1H-imidazo [4,5-b] pyridine (20 milligrams) in 0.5 milliliter of acetone was treated with 0.1 gram of sodium iodide in 0.5 milliliter of acetone. The reaction mixture was shaken with ether and bicarbonate solution. The ether portion was dried over magnesium sulfate and evaporated, yielding 10 milligrams (about 73 percent) of 6-chloro-2-(trifluoromethyl)-1H-imidazo [4,5-b] pyridine.

Workup

  1. dry with materialThe ether portion was dried over magnesium sulfate
  2. customevaporated

Sources & evidence

ORD record
ord-fde4c1ece5ef45c68a2011d043d95a1d
Source dataset
uspto-grants-1977_06
Patent number
US04031107

Linked notes

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