Cesium carbonate → HCID 86709753, compound

HRID 1400283Notes

Reaction equation

HRID 1400283 reaction equation
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].FC(F)(F)S(O[C:59]1[CH:68]=[CH:67][C:66]2[C:61](=[CH:62][CH:63]=[CH:64][CH:65]=2)[C:60]=1[Cl:69])(=O)=O.[NH2:72][CH2:73][CH2:74][NH:75][C:76](=[O:82])[O:77][C:78]([CH3:81])([CH3:80])[CH3:79]>CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1>[Cl:69][C:60]1[C:61]2[C:66](=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH:67]=[CH:68][C:59]=1[NH:72][CH2:73][CH2:74][NH:75][C:76](=[O:82])[O:77][C:78]([CH3:80])([CH3:79])[CH3:81]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 187201N-BOC-ethylenediamineHCID 634876Binap, (A+-)-HCID 12095458HCID 12095458, compound

Product 1

HCID 86709753HCID 86709753, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

An oven-dried microwave vial was evacuated and backfilled with argon. The vial was charged with Pd(OAc)2 (25 mg 0.113 mmol, 10 mol % Pd), BINAP (112 mg, 0.17 mmol, 15 mol %), and Cs2CO3 (733 mg, 2.25 mmol) and evacuated and backfilled with argon. The flask was capped with a rubber septum, and dry dioxane (6 mL), 1-chloronaphthalen-2-yl trifluoromethanesulfonate (350 mg, 1.13 mmol), and tert-butyl (2-aminoethyl)carbamate (361 mg, 2.25 mmol) were added through the septum. Then, the reaction vial was sealed and placed in the microwave reactor and irradiated for 2 h at 150° C. until the starting materials had been completely consumed as judged by TLC and GC analysis. The crude product was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate 99:1 to 90:10 as eluent) to afford tert-butyl {2-[(1-chloronaphthalen-2-yl)amino]ethyl}carbamate as a whitish solid in 48% yield.

Workup

  1. customAn oven-dried microwave vial was evacuated
  2. customevacuated
  3. additionwere added through the septum
  4. customThen, the reaction
  5. customvial was sealed
  6. customirradiated for 2 h at 150° C. until the starting materials
  7. customhad been completely consumed
  8. customThe crude product was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate 99:1 to 90:10 as eluent)

Sources & evidence

ORD record
ord-50e8583c59424c9e9d292214ac41880d
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Reaction notes

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