Cesium carbonate → 3-Cyclopropylaniline

HRID 2200156Notes

Reaction equation

HRID 2200156 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH:9]1(B(O)O)[CH2:11][CH2:10]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:9]1([C:2]2[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=2)[NH2:5])[CH2:11][CH2:10]1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 115623-BromoanilineHCID 2760897Cyclopropylboronic acid

Product 1

HCID 120321393-CyclopropylanilineYield 38.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Stir the mixture of 3-bromoaniline (400 mg, 2.35 mmol), cyclopropylboronic acid (240 mg, 2.79 mmol), tetrakis(triphenylphosphine)palladium(0) (140 mg, 0.12 mmol), cesium carbonate (1.5 g, 4.60 mmol) in dioxane (5 mL) and water (0.3 mL) under nitrogen atmosphere for 17 hrs at 100° C. Cool the reaction to room temperature, filter and concentrate the filtrate under reduced pressure. Purify by flash chromatography (silica gel, EtOAc:PE=3:7) to afford the title compound (120 mg, 38.8%). MS: (M+1): 134.0.

Workup

  1. temperatureCool
  2. customthe reaction to room temperature
  3. filtrationfilter
  4. concentrationconcentrate the filtrate under reduced pressure
  5. customPurify by flash chromatography (silica gel, EtOAc:PE=3:7)

Sources & evidence

ORD record
ord-5c2c5f09888e4767813df027867b7133
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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