Triethylamine → HCID 68843166, compound

HRID 660499Notes

Reaction equation

HRID 660499 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](I)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:18](=[O:29])[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:30]([C:32]1[S:36][CH:35]=[N:34][CH:33]=1)=[CH2:31].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CC#N.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:31]=[CH:30][C:32]2[S:36][CH:35]=[N:34][CH:33]=2)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:18](=[O:29])[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 136785515-vinylthiazoleHCID 667569375-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Product 1

HCID 68843166HCID 68843166, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A pressure vessel is charged with 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (828 mg, 1.52 mmol), 5-vinyl thiazole (186 mg, 1.68 mmol), triethylamine (0.32 mL, 2.28 mmol) and tri-o-tolylphosphine (37 mg, 0.12 mmol) in CH3CN (1.5 mL). The vessel is degassed and palladium(II) acetate (6.80 mg, 0.03 mmol) is added. The vessel is sealed and heated at 80° C. for 20 h. The reaction mixture is concentrated and dissolved in EtOAc, washed with 1N HCl , dried over MgSO4 and concentrated. The residue is purified by column chromatography to afford the title compound as a yellow solid; (M+H)+=528.

Workup

  1. customThe vessel is degassed
  2. customThe vessel is sealed
  3. concentrationThe reaction mixture is concentrated
  4. dissolutiondissolved in EtOAc
  5. washwashed with 1N HCl
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-6cbac1743dbe470cb6b6c1e60693ae14
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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