Acetic Acid → HCID 9909300, compound

HRID 609587Notes

Reaction equation

HRID 609587 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.C([Li])CCC.C(O)(=O)C.Br[C:17]1[C:23](=[O:24])[C:22]([N:25]2[CH2:30][CH2:29][N:28]([CH2:31][C:32]3[CH:40]=[CH:39][C:38]4[O:37][CH2:36][O:35][C:34]=4[CH:33]=3)[CH2:27][CH2:26]2)=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1.[Cl-].[Cl-].[Zn+2].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.[Pd]>[CH2:31]([N:28]1[CH2:27][CH2:26][N:25]([C:22]2[C:23](=[O:24])[C:17]([C:2]3[S:3][CH:4]=[CH:5][CH:6]=3)=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:30][CH2:29]1)[C:32]1[CH:40]=[CH:39][C:38]2[O:37][CH2:36][O:35][C:34]=2[CH:33]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 138512-BromothiopheneHCID 9865867HCID 9865867, compoundHCID 178418339Butyllithium

Product 1

HCID 9909300HCID 9909300, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-bromothiophene (1.0 g, 6.1 mmol) in tetrahydrofuran (50 mL) at -78° C., was added n-butyl lithium (1.6 M in cyclohexane, 4.0 mL) and the resulting solution was stirred for 5 minutes. At this time, ZnCl2 (0.5 M in THF, 20 mL) was added and the solution was warmed to room temperature over 2 hours. To the reaction mixture was then added palladium tetrakis(triphenylphosphine) (200 mg) and a solution of the acetic acid salt of 7-bromo-2-(4-piperonyl-1-piperazinyl)-2,4,6-cycloheptatriene-1-one (300 mg, 0.74 mmol, example 1b) in tetrahydrofuran (5 mL) and the resulting mixture was refluxed for 18 hours. The reaction was quenched with a saturated aqueous ammonium chloride solution and the product, extracted into methylene chloride (3×200 mL). The crude product was purified by silica gel chromatography to provide the title compound as a dark yellow oil (50 mg, 50%).

Workup

  1. customThe reaction was quenched with a saturated aqueous ammonium chloride solution
  2. extractionthe product, extracted into methylene chloride (3×200 mL)
  3. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3bdb0fc8943e4ac58b5540442e924e48
Source dataset
uspto-grants-1999_12
Patent number
US05998414

Reaction notes

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