Triethylamine → HCID 14612247, compound

HRID 1350374Notes

Reaction equation

HRID 1350374 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.I[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[C:37]1([CH3:64])[CH:42]=[CH:41][C:40]([S:43]([N:46]2[CH2:51][CH2:50][N:49]([S:52]([C:55]3[CH:60]=[CH:59][C:58]([CH3:61])=[CH:57][CH:56]=3)(=[O:54])=[O:53])[CH2:48][CH:47]2[CH:62]=[CH2:63])(=[O:45])=[O:44])=[CH:39][CH:38]=1>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[CH:62]([CH:47]1[CH2:48][N:49]([S:52]([C:55]2[CH:56]=[CH:57][C:58]([CH3:61])=[CH:59][CH:60]=2)(=[O:53])=[O:54])[CH2:50][CH2:51][N:46]1[S:43]([C:40]1[CH:39]=[CH:38][C:37]([CH3:64])=[CH:42][CH:41]=1)(=[O:44])=[O:45])=[CH:63][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[C:37]1([CH3:64])[CH:42]=[CH:41][C:40]([S:43]([N:46]2[CH2:51][CH2:50][N:49]([S:52]([C:55]3[CH:60]=[CH:59][C:58]([CH3:61])=[CH:57][CH:56]=3)(=[O:54])=[O:53])[CH2:48][CH:47]2[CH:62]=[CH2:63])(=[O:44])=[O:45])=[CH:39][CH:38]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11575IodobenzeneHCID 80271Tri-o-tolylphosphineHCID 14612247HCID 14612247, compound

Product 2

HCID 14612247HCID 14612247, compoundHCID 69489692HCID 69489692, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Combine tri-o-tolylphosphine (72 mg, 0.24 mmol), palladium acetate (12 mg, 0.05 mmol), triethylamine (0.22 mL, 1.6 mmol), iodobenzene (0.20 mL, 1.83 mmol), 1,4-bis-(toluene-4-sulfonyl)-2-vinyl-piperazine (320 mg, 0.76 mmol) and acetonitrile (8 mL) in a sealable vessel and purge with nitrogen. Seal the vessel and heat at 110° C. After 21 hours 45 minutes, cool to ambient temperature and dilute with ethyl acetate. Filter and discard the solids. Concentrate the filtrate and purify by silica gel chromatography using ethyl acetate-hexanes (0–30%) as the eluent to give a 8:1 ratio of the title compound to 1,4-bis-(toluene-4-sulfonyl)-2-vinyl-piperazine: mass spectrum (ion spray): m/z=497 (M+1); 1H NMR(DMSO-d6): δ7.59 (d, 2H), 7.53 (d, 2H), 7.42 (d, 2H), 7.19–7.36 (m, 7H), 6.48 (d, 1H), 6.08 (dd, 1H), 4.62 (m, 1H), 3.70 (br d, 1H), 3.52 (m, 2H), 3.29 (dd, 1H), 2.41 (s, 3H), 2.29–2.32 (m, 1H), 2.26 (s, 3H), 2.12 (dd, 1H).

Workup

  1. customSeal the vessel
  2. temperaturecool to ambient temperature
  3. filtrationFilter
  4. concentrationConcentrate the filtrate
  5. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-bc2bde686a4a4305bd18ef1b69504750
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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