Cesium carbonate → HCID 59496674, compound

HRID 449520Notes

Reaction equation

HRID 449520 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[Cl:18][C:19]1[CH:20]=[CH:21][C:22](F)=[C:23]([CH:26]=1)[C:24]#[N:25].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.C(OCC)(=O)C>[C:13]([O:12][C:11](=[O:17])[NH:10][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:1][C:22]2[CH:21]=[CH:20][C:19]([Cl:18])=[CH:26][C:23]=2[C:24]#[N:25])[CH:3]=1)[CH3:9])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 936535-Chloro-2-fluorobenzonitrileHCID 20791804HCID 20791804, compound

Product 1

HCID 59496674HCID 59496674, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

tert-Butyl [1-(3-hydroxyphenyl)ethyl]carbamate (0.025 g, 0.11 mmol) was dissolved in acetonitrile (1.0 mL) with 5-chloro-2-fluorobenzonitrile (Aldrich, Cat. #548693) (0.034 g, 0.22 mmol) and cesium carbonate (0.073 g, 0.22 mmol) in a sealed tube. The reaction was heated to 100° C. for 2 h. and was complete. The reaction was taken up in ethyl acetate, filtered and concentrated under reduced pressure to give crude tert-butyl{1-[3-(4-chloro-2-cyanophenoxy)phenyl]ethyl}carbamate (0.040 g) as a clear oil. Analytical LCMS (M+H-Boc)+: m/z=272.9.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-02673f20245347f1a9e457b083f20036
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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