Iodobenzene → HCID 68501857, compound

HRID 1176514Notes

Reaction equation

HRID 1176514 reaction equation
CC(C)([O-])C.[Na+].[CH3:7][O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:17]2[CH:18]=[C:19]([CH2:22][O:23][CH:24]3[CH:29]([C:30]4[CH:35]=[CH:34][C:33]([O:36][C@H:37]5[CH2:41][CH2:40][NH:39][CH2:38]5)=[CH:32][CH:31]=4)[CH2:28][CH2:27][N:26]([C:42]([O:44][CH2:45][C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)=[O:43])[CH2:25]3)[CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C:13]1=[O:52].I[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>O1CCOCC1>[CH3:7][O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:17]2[CH:18]=[C:19]([CH2:22][O:23][CH:24]3[CH:29]([C:30]4[CH:31]=[CH:32][C:33]([O:36][C@H:37]5[CH2:41][CH2:40][N:39]([C:54]6[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=6)[CH2:38]5)=[CH:34][CH:35]=4)[CH2:28][CH2:27][N:26]([C:42]([O:44][CH2:45][C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)=[O:43])[CH2:25]3)[CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C:13]1=[O:52]

Participants

6

Reactant 4

HCID 11575IodobenzeneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 68502007HCID 68502007, compound

Product 1

HCID 68501857HCID 68501857, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The mixture of 0.106 g of sodium tert-butoxide, 0.500 g of benzyl 3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-[4-(pyrrolidin-3(S)-yloxy)phenyl]piperidine-1-carboxylate, 0.106 ml iodobenzene and 8.5 ml of dioxane is initially charged under argon in a Schlenk apparatus with stirring. The mixture is admixed with the solution of 0.028 g of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene and tris(dibenzylidenacetone)dipalladium(0) in 2.5 ml of dioxane (prepared in a Schlenk apparatus under argon) and stirred at 60° C. for 3 hours. The reaction mixture is cooled, poured onto ice-water (70 ml) and extracted with tert-butyl methyl ether (2×70 ml). The organic phases are washed with brine (70 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a brown foam from the residue by means of flash chromatography (SiO2 60F). Rf=0.20 (1:1 EtOAc-heptane). Rt=5.88.

Workup

  1. additionis initially charged under argon in a Schlenk apparatus
  2. stirringstirred at 60° C. for 3 hours
  3. temperatureThe reaction mixture is cooled
  4. additionpoured onto ice-water (70 ml)
  5. extractionextracted with tert-butyl methyl ether (2×70 ml)
  6. washThe organic phases are washed with brine (70 ml)
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-8a9b653df88048a78ac7acd938f67e98
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

Loading…