Lithium Chloride → N-{[7-(2-pyridinyl)-2-(trifluoromethyl)-1H-indol-5-yl]methyl}-6-(trifluoromethyl)-3-pyridinecarboxamide

HRID 73228

Reaction equation

HRID 73228 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][NH:13][C:14](C1C=CC(C(F)(F)F)=CN=1)=[O:15])=[CH:7][C:6]=2Br.C([Sn](CCCC)(CCCC)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)CCC.[Cl-].[Li+]>C1(C)C=CC=CC=1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[C:6]1[CH:7]=[C:8]([CH2:12][NH:13][C:14]([C:37]2[CH:36]=[N:35][C:34]([C:2]([F:28])([F:27])[F:1])=[CH:39][CH:38]=2)=[O:15])[CH:9]=[C:10]2[C:5]=1[NH:4][C:3]([C:2]([F:28])([F:27])[F:1])=[CH:11]2

Participants

7

Reactant 3

HCID 433294Lithium ChlorideHCID 6077842-(Tributylstannyl)pyridineHCID 44255926N-[(2-Trifluoromethyl-7-bromo-1H-indol-5-yl)methyl]-5-(trifluoromethyl)-2-pyridinecarboxamide2×

Product 1

HCID 46937537N-{[7-(2-pyridinyl)-2-(trifluoromethyl)-1H-indol-5-yl]methyl}-6-(trifluoromethyl)-3-pyridinecarboxamide

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

In a 2 mL microwave reactor vial N-[(2-Trifluoromethyl-7-bromo-1H-indol-5-yl)methyl]-5-(trifluoromethyl)-2-pyridinecarboxamide (Intermediate 6, 50 mg), 2-tri-n-butylstannyl pyridine (Frontier Scientific Inc., 79 mg), lithium chloride (45.5 mg), copper(I) iodide (2.04 mg) and tetrakis(triphenylphosphine)palladium(0) (12.39 mg) were stirred in Toluene (2 mL) and de-gassed using argon gas. The reaction mixture was then heated in a microwave reactor at 140° C. for 3 h. The reaction mixture was poured into water (20 mL) and extracted with ethyl acetate (40 mL). The organic extract was then washed with water (2×20 mL), dried (MgSO4), filtered and the solvent removed. The resulting residues were purified by MDAP and evaporated to dryness to give the title compound as an off white solid (25.7 mg);

Workup

  1. customde-gassed
  2. additionThe reaction mixture was poured into water (20 mL)
  3. extractionextracted with ethyl acetate (40 mL)
  4. extractionThe organic extract
  5. washwas then washed with water (2×20 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed
  9. customThe resulting residues were purified by MDAP
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-78ed8a90d77d44deb77de4c649b46dd3
Source dataset
uspto-grants-2014_09
Patent number
US08829031B2

Linked notes

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