Triethylamine → 7-(3-Methylaminosulfonylphenyl)-1-(4-methyl-1-piperazinyl)naphthalene

HRID 235131Notes

Reaction equation

HRID 235131 reaction equation
C[Sn](C)(C)[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:5][CH:4]=1.[CH3:22][NH:23][S:24]([C:27]1[CH:28]=[C:29](Br)[CH:30]=[CH:31][CH:32]=1)(=[O:26])=[O:25].C(N(CC)CC)C.[Cl-].[Li+]>CN(C=O)C.[Pd](Cl)Cl.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>[CH3:22][NH:23][S:24]([C:27]1[CH:28]=[C:29]([C:3]2[CH:12]=[C:11]3[C:6]([CH:7]=[CH:8][CH:9]=[C:10]3[N:13]3[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)=[CH:5][CH:4]=2)[CH:30]=[CH:31][CH:32]=1)(=[O:25])=[O:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 433294Lithium Chloride2×HCID 72132653-bromo-N-methylbenzene-1-sulfonamideHCID 221156087-Trimethylstannyl-1-(4-methyl-1-piperazinyl)-naphthalene

Product 1

HCID 189675037-(3-Methylaminosulfonylphenyl)-1-(4-methyl-1-piperazinyl)naphthalene

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

7-Trimethylstannyl-1-(4-methyl-1-piperazinyl)-naphthalene (0.25 g, 0.67 mmol), 3-methylaminosulfonyl-1-bromobenzene (0.18 g, 0.72 mmol), triethylamine (0.45 mL, 3.23 mmol), lithium chloride (0.088 g, 2.07 mmol), and bis (triphenylphosphine) palladium chloride (0.025 g, 0.036 mmol) were combined in DMF (12.5 mL) and heated to 110° to 110° C. for 45 minutes. The reaction was cooled to room temperature and 1 N aqueous lithium chloride (20 mL) was added. The mixture was extracted with ether (2x). The combined organic layer was washed with 1N lithium chloride and brine; then it was dried over magnesium sulfate and concentrated to an orange oil. Flash chromatography on silica gel (1×6 inches) with an ethyl acetate/hexane gradient of from 50 to 75% followed by continued elution with ethyl acetate and finally 5% methanol/ethyl acetate 0.11 g (42%) of the title product. The sample was recrystallized from ethyl acetate for analysis: mp 147.5°-148° C. Analysis calculated for C22H25N3O2S: C, 66.81; H, 6.31; N, 10.62. Found: C, 66.32; H, 6.16; N, 10.41.

Workup

  1. temperatureheated to 110° to 110° C. for 45 minutes
  2. extractionThe mixture was extracted with ether (2x)
  3. washThe combined organic layer was washed with 1N lithium chloride and brine
  4. dry with materialthen it was dried over magnesium sulfate
  5. concentrationconcentrated to an orange oil
  6. washFlash chromatography on silica gel (1×6 inches) with an ethyl acetate/hexane gradient of from 50 to 75% followed by continued elution with ethyl acetate and finally 5% methanol/ethyl acetate 0.11 g (42%) of the title product
  7. customThe sample was recrystallized from ethyl acetate for analysis

Sources & evidence

ORD record
ord-55ef8c79fecf408fa2af79218c67052f
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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