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2-(Tributylstannyl)-1,3-thiazole → 5-Acetyl-1-(3-(2-thiazolyl)phenyl)benzimidazole

HRID 581961
Notes
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Reaction equation

HRID 581961 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[CH:9][N:10]=1)CCC.[C:19]([C:22]1[CH:37]=[CH:36][C:25]2[N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31](Br)[CH:30]=3)[CH:27]=[N:28][C:24]=2[CH:23]=1)(=[O:21])[CH3:20]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:19]([C:22]1[CH:37]=[CH:36][C:25]2[N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:6]4[S:7][CH:8]=[CH:9][N:10]=4)[CH:30]=3)[CH:27]=[N:28][C:24]=2[CH:23]=1)(=[O:21])[CH3:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 540303071-(1-(3-bromophenyl)-1H-benzo[d]imidazol-5-yl)ethanone

Product 1

HCID 537406525-Acetyl-1-(3-(2-thiazolyl)phenyl)benzimidazoleYield 97.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of (33) (3.6 g, 9.7 mmol) in dry THF (20 ml) was added 5-acetyl-1-(3-bromophenyl)benzimidazole (1.5 g, 4.8 mmol) and (PPh3)2PdCl2 (340 mg, 0.48 mmol) under argon. The reaction mixture was stirred at 80° C. for 24 hr in a 50 ml sealed tube. After cooling the mixture was concentrated, triturated with water (100 ml) and extracted with CH2Cl2 (200 ml×3). The extract was washed with brine, dried and concentrated under reduced pressure. The residue was washed with ether to afford crystaline (34) (1.5 g, 89%).

Workup

  1. customsealed tube
  2. temperatureAfter cooling the mixture
  3. concentrationwas concentrated
  4. customtriturated with water (100 ml)
  5. extractionextracted with CH2Cl2 (200 ml×3)
  6. washThe extract was washed with brine
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. washThe residue was washed with ether

Sources & evidence

ORD record
ord-18d5d5eb6be0453a85f7fbb570da8450
Source dataset
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05922724

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes