Cesium carbonate → HCID 66798493, compound

HRID 1193410Notes

Reaction equation

HRID 1193410 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](Cl)[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][N:17]([CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:18](=[O:27])[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+].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.C(Cl)Cl.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]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N:31]2[CH2:30][CH2:29][CH:28]([N:17]([CH3:16])[C:18](=[O:27])[O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:33][CH2:32]2)[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 18677746Benzyl methyl(piperidin-4-yl)carbamateHCID 543280722-(Benzyloxy)-4-chloropyridine

Product 1

HCID 66798493HCID 66798493, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(benzyloxy)-4-chloropyridine (800 mg, 3.653 mmol, 1.0 eq), benzyl methyl(piperidin-4-yl)carbamate (stage 3 AMN-52) (0.997 g, 4.018 mmol, 1.1 eq) and Cs2CO3 (2.374 g, 7.306 mmol, 2.0 eq) in toluene (10 ml) was degassed for 15 minutes with nitrogen. Pd2(dba)3 (166 mg, 0.182 mmol, 0.05 eq) and Xantphos (105 mg, 0.182 mmol, 0.05 eq) were then added and stirring was carried out for 14 hours at 90° C. After monitoring by TLC, the mixture was diluted with DCM (150 ml), washed with water (70 ml) and sat. NaCl solution (70 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 2.0% MeOH in DCM). Yield: 32% (500 mg, 1.160 mmol)

Workup

  1. customwas degassed for 15 minutes with nitrogen
  2. washwashed with water (70 ml) and sat. NaCl solution (70 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (silica gel, 2.0% MeOH in DCM)

Sources & evidence

ORD record
ord-5628d11088e4471fb10f19efba98935a
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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