Sodium Hydroxide → HCID 22717667, compound

HRID 1582544Notes

Reaction equation

HRID 1582544 reaction equation
I[C:2]1[S:6][C:5]([NH:7][C:8](=[O:19])[C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[N:4][C:3]=1[C:20]([F:23])([F:22])[F:21].[OH-].[Na+].[F:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1>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>[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]2[S:6][C:5]([NH:7][C:8](=[O:19])[C:9]3[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=3)=[N:4][C:3]=2[C:20]([F:23])([F:22])[F:21])=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2856454-Fluorophenylboronic acidHCID 85964633HCID 85964633, compound

Product 1

HCID 22717667HCID 22717667, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

N-(5-Iodo-4-trifluoromethylthiazol-2-yl)-4-trifluoromethylbenzamide (0.8 g), powdered sodium hydroxide (0.29 g), tetrakis(triphenylphosphine)-palladium(0) (0.2 g) and 4-fluorophenylboronic acid (0.24 g) were mixed together in tetrahydrofuran (30 ml). The resulting suspension was refluxed for 8 hr with stirring. The solvent was removed under reduced pressure and the residue was mixed with water then extracted with chloroform. The chloroform layer was dried over magnesium chloride and the solvent was removed under reduced pressure. The solid remained was recrystallized from methanol to give N-(5-(4-fluorophenyl)-4-trifluoromethylthiazol-2-yl)-4-trifluoromethylbenzamide as slightly gray needles (0.55 g), m. p. 203-205° C.

Workup

  1. temperatureThe resulting suspension was refluxed for 8 hr
  2. customThe solvent was removed under reduced pressure
  3. additionthe residue was mixed with water
  4. extractionthen extracted with chloroform
  5. dry with materialThe chloroform layer was dried over magnesium chloride
  6. customthe solvent was removed under reduced pressure
  7. customThe solid remained was recrystallized from methanol

Sources & evidence

ORD record
ord-9de87811978b46ba8452dd7db3a618cc
Source dataset
uspto-grants-2004_05
Patent number
US06737382B1

Reaction notes

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