Triethylamine → Tert-butyl 3-((2-amino-5-bromophenyl)ethynyl)pyrrolidine-1-carboxylate

温度

70 °C

4-Bromo-2-iodoaniline (3.88 g, 19.88 mmol), tert-butyl 3-ethynylpyrrolidine-1-carboxylate (4.90 g, 16.45 mmol), CuI (65 mg, 0.34 mmol, 2 mol %) and Pd(PPh3)2Cl2 (115 mg, 0.16 mmol, 1 mol %) were mixed together under argon in a heat-gun dried flask. Acetonitrile (17 mL) and NEt3 (4.60 mL, 33.00 mmol) were added to the mixture and reaction was heated at 70° C. for 1.5 h. TLC showed complete consumption of the alkyne. Acetonitrile was concentrated under reduced pressure and EtOAc (100 mL) was added to the residue. Triethylamine salt was filtered off and washed with EtOAc. Mother liquor was concentrated and residue was purified by column chromatography using EtOAc/hexanes (gradient 0-40%) to afford tert-butyl 3-((2-amino-5-bromophenyl)ethynyl)pyrrolidine-1-carboxylate (5.69 g) in 95% yield.

1. customdried flask
2. customconsumption of the alkyne
3. concentrationAcetonitrile was concentrated under reduced pressure and EtOAc (100 mL)
4. additionwas added to the residue
5. filtrationTriethylamine salt was filtered off
6. washwashed with EtOAc
7. concentrationMother liquor was concentrated
8. customresidue was purified by column chromatography

ORDレコード

ord-0dc851f2de414b0eb8f0bf979c673158

出典データセット

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09409905B2