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Water → HCID 22049705, compound

HRID 1830917
Notes
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Reaction equation

HRID 1830917 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:19]=3[C:20]([F:23])([F:22])[F:21])[S:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(N(CC)CC)C.C1[CH2:35][O:34][CH2:33][CH2:32]1.[OH2:36]>C(O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[N:10]=[C:11]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:19]=3[C:20]([F:23])([F:22])[F:21])[S:12][CH:13]=2)=[CH:3][C:2]=1[C:35]([O:34][CH2:33][CH3:32])=[O:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 22049737HCID 22049737, compound

Product 1

HCID 22049705HCID 22049705, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst
HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst
HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

3-[4-(3-Bromo-4-fluorophenyl)-1,3-thiazol-2-yl]-4-(trifluoromethyl)pyridine (1.48 g), 1,1′-bis(diphenylphosphino)ferrocene (680 mg), palladium acetate (270 mg) and triethylamine (0.77 ml) were suspended in a mixture of ethanol (15 ml)/THF (15 ml), and the mixture was vigorously stirred at 70° C. for 3 hrs at 5 atm under a carbon monoxide atmosphere. The reaction mixture was added to water and extracted with ethyl acetate. The organic layer was dried and concentrated. The residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=19:1–1:1) for purification and recrystallized from ethyl acetate-diisopropyl ether to give the title compound (1.17 g) as colorless powder crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=19:1–1:1) for purification
  5. customrecrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-d5848f8c93744f9fa49f181a35a8c3a9
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07067537B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes