Cesium carbonate → HCID 68817329, compound

HRID 1436534Notes

Reaction equation

HRID 1436534 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([CH:10]2[O:15][CH2:14][CH2:13][CH2:12][O:11]2)[N:7]=[C:6](Cl)[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C@@H:70]([NH2:74])([CH2:72][CH3:73])[CH3:71]>C1(C)C=CC=CC=1.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([CH:10]2[O:15][CH2:14][CH2:13][CH2:12][O:11]2)[N:7]=[C:6]([NH:74][C@H:70]([CH2:72][CH3:73])[CH3:71])[CH:5]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 67137532-Butanamine, (S)-HCID 86614999HCID 86614999, compound

Product 1

HCID 68817329HCID 68817329, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

Dissolve 2-chloro-6-[1,3]dioxan-2-yl-isonicotinic acid methyl ester (150 mg, 0.6 mmol), palladium (II) acetate (7.0 mg, 0.03 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (20 mg, 0.03 mmol) and cesium carbonate (482 mg, 1.3 mmol) in toluene (2 mL) in a previously degassed sealed vessel. Flush the mixture with nitrogen gas. Add (S)-(+)-sec-butylamine (0.074 mL, 0.74 mmol) and heat the sealed mixture overnight at 100° C. Cool to room temperature, dilute with diethyl ether and filter through filtering agent. Concentrate the filtrate and purify (silica gel chromatography, eluting with 0:100 to 20:80 ethyl acetate:hexanes) to give the title compound (68%).

Workup

  1. customa previously degassed
  2. customsealed vessel
  3. customFlush the mixture with nitrogen gas
  4. filtrationfilter
  5. filtrationthrough filtering agent
  6. concentrationConcentrate the filtrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with 0:100 to 20:80 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-8dcdfabd7088481fb0e71954ededf6c6
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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