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Potassium Hydroxide → 1-(6-Chloronaphth-2-ylsulphonyl)-4-[4-(3-pyridyl)benzoyl]piperazine

HRID 586209
Notes
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Reaction equation

HRID 586209 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:29])[C:22]3[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=3)[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.C(B(CC)[C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1)C.[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.CCOC(C)=O.[Pd].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>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:29])[C:22]3[CH:27]=[CH:26][C:25]([C:33]4[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=4)=[CH:24][CH:23]=3)[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 14797Potassium HydroxideHCID 6428513-(Diethylboryl)pyridineHCID 223297181-(6-Chloronaphth-2-ylsulphonyl)-4-(4-iodobenzoyl)piperazine

Product 1

HCID 120510341-(6-Chloronaphth-2-ylsulphonyl)-4-[4-(3-pyridyl)benzoyl]piperazineYield 38.5%

Reagents, catalysts & solvents 4

HCID 74236
Tetrabutylammonium Bromide
Catalyst
HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

1-(6-Chloronaphth-2-ylsulphonyl)-4-(4-iodobenzoyl)piperazine (920 mg, 1.7 mmol), diethyl 3-pyridylborane (250 mg, 1.7 mmol), tetrabutyl ammonium bromide (110 mg, 0.34 mmol), tetrakis(triphenylphosphine) palladium (0) (69 mg, 0.06 mmol) and potassium hydroxide (286 mg, 5.1 mmol) were refluxed in dry tetrahydrofuran (100 mL) for two hours under an atmosphere of nitrogen. The reaction mixture was allowed to cool to room temperature then concentrated in vacuo. The resulting solid was subjected to flash chromatography (SiO2: 100% CH2Cl2, 50% EtOAc/Hexane, 100% EtOAc) to yield an oil. The oil was dissolved in EtOAc (100 mL) and washed with saturated sodium hydrogen carbonate solution (100 mL). The EtOAc layer was separated, dried over MgSO4, filtered and concentrated in vacuo to yield an off white foam which was triturated with hexane. This solid was subjected to chromatography (SiO2: 40%, 50% 60%, 70% EtOAc/Hexane) to yield 1-(6-chloronaphth-2-ylsulphonyl)-4-[4-(3-pyridyl)benzoyl]piperazine as a white solid (322.4 mg); 1H NMR (DMSO-d6) δ=3.1 ppm (s,4H), δ=3.6 ppm (s,4H), δ=7.46 ppm (d,2H), δ=7.5 to 7.67 ppm (m,1H), δ=7.70 to 7.79 ppm (m,3H), δ=7.83 pmm (dd,1H), δ=8.09 ppm (dt,1H), δ=8.15 ppm to 8.31 ppm (m,3H), δ=8.50 ppm (s,1H), δ=8.60 ppm (dd,1H), δ=8.90 ppm (d,1H); MS (M+H)+ 492.

Workup

  1. concentrationthen concentrated in vacuo
  2. customto yield an oil
  3. washwashed with saturated sodium hydrogen carbonate solution (100 mL)
  4. customThe EtOAc layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto yield an off white foam which
  9. customwas triturated with hexane

Sources & evidence

ORD record
ord-7ac7282c30f0422e82f52c9019765023
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06936610B2

Reaction notes

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