Cesium carbonate → HCID 11617146, compound

HRID 2244410Notes

Reaction equation

HRID 2244410 reaction equation
C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.Cl.Br[C:45]1[CH:50]=[CH:49][N:48]=[CH:47][CH:46]=1.[Cl:51][C:52]1[CH:53]=[C:54]([NH:58][C:59]([C:61]2[N:62]=[C:63]([CH3:67])[S:64][C:65]=2[NH2:66])=[O:60])[CH:55]=[CH:56][CH:57]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[Cl:51][C:52]1[CH:53]=[C:54]([NH:58][C:59]([C:61]2[N:62]=[C:63]([CH3:67])[S:64][C:65]=2[NH:66][C:45]2[CH:50]=[CH:49][N:48]=[CH:47][CH:46]=2)=[O:60])[CH:55]=[CH:56][CH:57]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 881004-Bromopyridinium chlorideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 11608689HCID 11608689, compound

Product 1

HCID 11617146HCID 11617146, compoundYield 9.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Dry dioxane (1.00 ml) was added to a sealed microwave vial containing a mixture of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (0.015 g, 0.026 mmol), palladium dibenzylideneacetone chloroform complex (0.008 g, 0.008 mmol), 4-bromopyridine hydrochloride (0.03 g, 0.15 mmol), 5-amino-2-methyl-thiazole-4-carboxylic acid (3-chlorophenyl)-amide (0.05 g, 0.19 mmol) and cesium carbonate (0.18 g, 0.54 mmol). The mixture was stirred for 10 min, then irradiated in a microwave oven at 150° C. for 10 min. The volatiles were then removed under vacuum, and the residue was purified by flash chromatography (dichloromethane/methanol), yielding the title compound (0.005 g, 9%), as a yellow solid, MS (ISP): m/e=345.5 (M+H+).

Workup

  1. additioncontaining
  2. customirradiated in a microwave oven at 150° C. for 10 min
  3. customThe volatiles were then removed under vacuum
  4. customthe residue was purified by flash chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-80247028ff6f4775934cae8b140a26df
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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