Toluene → 1-Methyl-4-[3-(3-methyl-thiophen-2-yl)-4-nitro-phenyl]-piperazine

HRID 1427985Notes

Reaction equation

HRID 1427985 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].CC1(C)C(C)(C)OB([C:26]2[S:27][CH:28]=[CH:29][C:30]=2[CH3:31])O1.C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>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.CCOC(C)=O.C(O)C>[CH3:17][N:14]1[CH2:15][CH2:16][N:11]([C:4]2[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([C:26]3[S:27][CH:28]=[CH:29][C:30]=3[CH3:31])[CH:3]=2)[CH2:12][CH2:13]1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 117815411-(3-Bromo-4-nitrophenyl)-4-methylpiperazineHCID 455881254,4,5,5-Tetramethyl-2-(3-methylthiophen-2-yl)-1,3,2-dioxaborolane

Product 1

HCID 594638211-Methyl-4-[3-(3-methyl-thiophen-2-yl)-4-nitro-phenyl]-piperazineYield 63%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a flask containing 1-(3-bromo-4-nitro-phenyl)-4-methyl-piperazine (68 mg, 0.2 mmol, as prepared in Example 4, step (a)), 4,4,5,5-tetramethyl-2-(3-methyl-thiophen-2-yl)-[1,3,2]dioxaborolane (61 mg, 0.27 mmol, as prepared in the previous step) and Pd(PPh3)4 (14 mg, 6 mol %) was charged toluene (3 mL), ethanol (3 mL) and 2M Na2CO3 (4 mL). The resultant mixture was heated at 80° C. for 2 h and then poured into EtOAc (25 mL). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. Purification by silica gel preparative thin layer chromatography (EtOAc) afforded 40 mg (63%) of the title compound as a light yellow solid. Mass spectrum (ESI, m/z): Calcd. for C16H19N3O2S, 318.1 (M+H). found 318.2.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by silica gel preparative thin layer chromatography (EtOAc)

Sources & evidence

ORD record
ord-2326cba781944fcba3a9f524ac4e46dc
Source dataset
uspto-grants-2015_01
Patent number
US08933091B2

Reaction notes

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