Sodium Carbonate → 2-[3,5-bis(trifluoromethyl)phenyl]-N-[6-chloro-4-(5-fluoro-2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamide

HRID 421197Notes

Reaction equation

HRID 421197 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([C:13]([CH3:27])([CH3:26])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([Cl:25])=[CH:22][C:23]=2I)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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>[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([C:13]([CH3:27])([CH3:26])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([Cl:25])=[CH:22][C:23]=2[C:36]2[CH:35]=[C:34]([F:37])[CH:33]=[CH:32][C:31]=2[CH3:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27831905-Fluoro-2-methylphenylboronic acidHCID 866241982-[3,5-bis(trifluoromethyl)phenyl]-N-(6-chloro-4-iodo-3-pyridinyl)-N,2-dimethylpropanamide

Product 1

HCID 592158892-[3,5-bis(trifluoromethyl)phenyl]-N-[6-chloro-4-(5-fluoro-2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamideYield 27%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-[3,5-bis(trifluoromethyl)phenyl]-N-(6-chloro-4-iodo-3-pyridinyl)-N,2-dimethylpropanamide (200 mg, 0.363 mmol), 2-methyl-5-fluorobenzene boronic acid (73 mg, 0.472 mmol), sodium carbonate (0.4 mL, 2M solution), tetrakistriphenylphosphinepalladium (4 mg, 0.00363 mmol) in dioxan were heated together in the microwave at 110° C. for 30 minutes. The mixture was partitioned between EtOAc and Brine. The Aqueous layer was extracted with EtOAc×3. The combined extracts were dried and evaporated. The residue was purified on a 12+M column eluting with Pet Et2O to 60% EtOAc/Pet Et2O to afford the title compound in a 27% yield.

Workup

  1. customThe mixture was partitioned between EtOAc and Brine
  2. extractionThe Aqueous layer was extracted with EtOAc×3
  3. customThe combined extracts were dried
  4. customevaporated
  5. customThe residue was purified on a 12+M column
  6. washeluting with Pet Et2O to 60% EtOAc/Pet Et2O

Sources & evidence

ORD record
ord-9f30110c04784a7dbfd937ad1c33f774
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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