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2-(3-Chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [2-(bicyclopropyl-1-ylcarbamoyl)-4-iodo-6-methyl-phenyl]-amide → 2-(3-Chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [2-(bicyclopropyl-1-ylcarbamoyl)-4-cyano-6-methyl-phenyl]-amide

HRID 1819275
Notes
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Reaction equation

HRID 1819275 reaction equation
[C:1]1([NH:7][C:8]([C:10]2[CH:15]=[C:14](I)[CH:13]=[C:12]([CH3:17])[C:11]=2[NH:18][C:19]([C:21]2[N:22]([C:30]3[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][N:31]=3)[N:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=2)=[O:20])=[O:9])([CH:4]2[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[C:37]([Cu])#[N:38]>O1CCCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]1([NH:7][C:8]([C:10]2[CH:15]=[C:14]([C:37]#[N:38])[CH:13]=[C:12]([CH3:17])[C:11]=2[NH:18][C:19]([C:21]2[N:22]([C:30]3[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][N:31]=3)[N:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=2)=[O:20])=[O:9])([CH:4]2[CH2:6][CH2:5]2)[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 578872022-(3-Chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [2-(bicyclopropyl-1-ylcarbamoyl)-4-iodo-6-methyl-phenyl]-amideHCID 178418546HCID 178418546, compound

Product 1

HCID 709604762-(3-Chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [2-(bicyclopropyl-1-ylcarbamoyl)-4-cyano-6-methyl-phenyl]-amideYield 101.2%

Reagents, catalysts & solvents 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3.29 g (5.23 mmol) 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [2-(bicyclopropyl-1 -ylcarbamoyl)-4-iodo-6-methyl-phenyl]-amide in 50 ml tetrahydrofuran is added 1.19 g (6.25 mmol) Cul, 0.30 g tetrakis(triphenylphosphine) palladium and 2.78 g (31.0 mmol) CuCN. The mixture is heated 1 h at 80° C. and turns dark green. After cooling down, the mixture is filtered on Hyflo and evaporated. The residue is dissolved in 15 ml DMF and poured into 100 ml water containing 5 g NaHCO3. After 30 min stirring, the crystals are filtered, washed with water and a mixture of hexane/acetone (1:3) to afford 2.8 g of the title compound.

Workup

  1. temperatureAfter cooling down
  2. filtrationthe mixture is filtered on Hyflo
  3. customevaporated
  4. dissolutionThe residue is dissolved in 15 ml DMF
  5. additionpoured into 100 ml water containing 5 g NaHCO3
  6. filtrationthe crystals are filtered
  7. washwashed with water
  8. additiona mixture of hexane/acetone (1:3)

Sources & evidence

ORD record
ord-62df47719f6049d1a931a7d7ec5facfb
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07601743B2

Reaction notes

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