1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 71736574, compound

HRID 1471785Notes

Reaction equation

HRID 1471785 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20](Cl)[CH:21]=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][S:25]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)(=[O:27])=[O:26].CC(C)([O-])C.[K+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20]([N:31]4[CH2:32][CH2:33][N:28]([S:25]([CH3:24])(=[O:27])=[O:26])[CH2:29][CH2:30]4)[CH:21]=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 7091611-(Methylsulfonyl)piperazineHCID 23665647Potassium tert-butoxideHCID 866748894-(5-Chlorofuro[2,3-c]pyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 71736574HCID 71736574, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

4-(5-Chloro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (80 mg) is added to a flask charged with a stir bar, N-methylsulfonyl-piperazine (47 mg), potassium tert-butoxide (63 mg), Xantphos (103 mg), tris(dibenzylideneacetone)-dipalladium(0) (54 mg), and toluene (3 mL). The mixture is sparged with Ar at room temperature for 10 min and then stirred at 110° C. overnight. After cooling the mixture to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated. The residue is purified by HPLC on reversed phase (methanol/water) to give the title compound. LC (method 5): tR=1.25 min; Mass spectrum (ESI+): m/z=465 [M+H]+.

Workup

  1. additioncharged with a stir bar
  2. customThe mixture is sparged with Ar at room temperature for 10 min
  3. temperatureAfter cooling the mixture to room temperature
  4. additionwater is added
  5. extractionthe resulting mixture is extracted with ethyl acetate
  6. dry with materialThe combined extracts are dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue is purified by HPLC on reversed phase (methanol/water)

Sources & evidence

ORD record
ord-3bea2380d3564ae9a98362de11f37442
Source dataset
uspto-grants-2015_04
Patent number
US09012456B2

Reaction notes

Loading…