Potassium Phosphate, Tribasic → 2-Amino-5-cyclopropylbenzonitrile

Combine 2-amino-5-bromo-benzonitrile (1.76 g, 8.95 mmol), cyclopropyl boronic acid (1.0 g, 11.64 mmol), tricyclohexylphosphine (0.251 g, 0.89 mmol) and potassium phosphate (6.65 g, 31.26 mmol) in a mixture of toluene (40 ml) and water (2 ml) and stir the mixture for 10 minutes. Add palladium acetate (0.101 g, 0.45 mmol) and heat the mixture to 100° C. After 3 hours add more tricyclohexylphosphine (0.251 g, 0.89 mmol) and palladium acetate (0.101 g, 0.45 mmol). After an additional 3 hours at 100° C., add 20 ml of water and extract the mixture three times with 50 ml of ethyl acetate. Combine the organic layers, dry over sodium sulfate and concentrate. Purify the residue using flash chromatography and eluting with a linear gradient starting with 100% hexanes and going to 70% hexanes: 30% ethyl acetate to obtain 0.988 g of the title compound (6.24 mmol, 70% yield) as a clear yellow oil: Mass spectrum (m/e): 159(M+1).

1. waitAfter an additional 3 hours at 100° C.
2. extractionextract the mixture three times with 50 ml of ethyl acetate
3. dry with materialdry over sodium sulfate
4. concentrationconcentrate
5. customPurify the residue
6. washeluting with a linear gradient

ORD record

ord-17deea1f29f04740acd3f98d43667bf6

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07384934B2