Binap, (A+-)- → 7-Chloro-1-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

温度

85 °C

1,7-Dichloro-5H-pyrido[4,3-b]indole-4-carbonitrile (5.0 g, 19 mmol), Pd2(dba)3 (0.873 g, 0.954 mmol), BINAP (1.782 g, 2.86 mmol), and sodium tert-butoxide (9.17 g, 95 mmol) were added to a flask. DME (125 ml) was added immediately followed by the addition of (1R)-1-cyclopropyl-2,2,2-trifluoroethanaminium chloride (5.02 g, 28.6 mmol). The reaction mixture was purged with nitrogen for 10 min, and heated at 85° C. overnight. The reaction was diluted with EtOAc, washed with water and brine, dried (magnesium sulfate), concentrated, and purified by flash chromatography to give the title compound. 1H NMR (600 MHz, CD3SOCD3) δ 12.63 (s, 1H); 8.56 (d, 1H); 8.40 (s, 1H); 7.54 (d, 1H); 7.47 (d, 1H); 7.36 (dd, 1H); 4.78 (m, 1H); 1.56 (m, 1H); 0.73 (m, 1H); 0.62 (m, 1H); 0.52 (m, 1H); 0.37 (m, 1H). LRMS (APCI) calc'd for (C17H12ClF3N4) [M+H]+, 365.1. found 365.0.

1. customThe reaction mixture was purged with nitrogen for 10 min
2. additionThe reaction was diluted with EtOAc
3. washwashed with water and brine
4. dry with materialdried (magnesium sulfate)
5. concentrationconcentrated
6. custompurified by flash chromatography

ORDレコード

ord-7515bf84c46c4af6abdb48f24f5d4d79

出典データセット

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08431569B2