Trifluoroacetic acid → HCID 67110747, compound

HRID 2080563Notes

Reaction equation

HRID 2080563 reaction equation
C(OC(=O)[N:7]([CH:17]1[CH2:19][CH:18]1[C:20]1[C:25]([Cl:26])=[CH:24][C:23]([Cl:27])=[CH:22][N:21]=1)[C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[I:15])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:26][C:25]1[C:20]([CH:18]2[CH2:19][CH:17]2[NH:7][C:8](=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[I:15])=[N:21][CH:22]=[C:23]([Cl:27])[CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67111501HCID 67111501, compound

Product 1

HCID 67110747HCID 67110747, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.800 g of tert-butyl[2-(3,5-dichloropyridin-2-yl)cyclopropyl](2-iodobenzoyl)carbamate (0.00075 mol) are dissolved in 7 ml of dichloromethane. 0.70 ml of trifluoroacetic acid are added to the reaction mixture which is left stirring at room temperature overnight. The reaction mixture is quenched with 15 ml of an aqueous solution of saturated sodium bicarbonate. After separation, the aqueous phase is extracted with dichloromethane (10 ml). The combined organic phases are dried over magnesium sulfate, filtered, concentrated to dryness and purified on silica to yield to 245 mg of N-[2-(3,5-dichloropyridin-2-yl)cyclopropyl]-2-iodobenzamide (65%).

Workup

  1. waitis left
  2. customThe reaction mixture is quenched with 15 ml of an aqueous solution of saturated sodium bicarbonate
  3. customAfter separation
  4. extractionthe aqueous phase is extracted with dichloromethane (10 ml)
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. custompurified on silica

Sources & evidence

ORD record
ord-a97ef9406a6e4067b4428fbf0f4b540a
Source dataset
uspto-grants-2011_04
Patent number
US07932396B2

Reaction notes

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