1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 66799298, compound

HRID 1193382Notes

Reaction equation

HRID 1193382 reaction equation
[CH3:1][N:2]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:19][O:20][C:21]1[CH:26]=[C:25](Br)[CH:24]=[CH:23][N:22]=1.C(O[Na])CCC.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>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:19][O:20][C:21]1[CH:26]=[C:25]([N:16]2[CH2:15][CH2:14][CH:13]([N:2]([CH3:1])[C:3](=[O:12])[O:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:18][CH2:17]2)[CH:24]=[CH:23][N:22]=1

Participants

7

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 140623094-Bromo-2-methoxypyridineHCID 18677746Benzyl methyl(piperidin-4-yl)carbamateHCID 178454433HCID 178454433, compound

Product 1

HCID 66799298HCID 66799298, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Benzyl methyl(piperidin-4-yl)carbamate (stage 3 AMN-52) (1.43 mmol, 1.0 eq.), 2-methoxy-4-bromopyridine and BuONa (411 mg, 4.29 mmol, 3.0 eq.) were taken up in toluene (20 ml) and degassed with argon. Xantphos (50 mg, 0.085 mmol, 0.06 eq.) and Pd2(dba)3 (26 mg, 0.028 mmol, 0.02 eq.) were then added and the mixture was heated for 16 hours at 90° C. After monitoring by TLC, the reaction mixture was concentrated and the residue was taken up in DCM (100 ml), washed with water and sat. NaCl solution (50 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 0.5% MeOH in DCM). Yield: 51% (260 mg, 0.732 mmol)

Workup

  1. customdegassed with argon
  2. concentrationthe reaction mixture was concentrated
  3. washwashed with water and sat. NaCl solution (50 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography (silica gel, 0.5% MeOH in DCM)

Sources & evidence

ORD record
ord-079376f175654289856fec06e7fff119
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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