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Stage #1: 4-amino-3-chloro-5-iodopyridine With sodium hydride In tetrahydrofuran for 0.0833333h; Inert atmosphere;
Stage #2: acetyl chloride In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #3: With water; lithium hydroxide In tetrahydrofuran for 0.5h; Inert atmosphere;
65%
Stage #1: 4-amino-3-chloro-5-iodopyridine; acetyl chloride With sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #2: With lithium hydroxide In tetrahydrofuran; water Inert atmosphere;
N-acetyl-N-(3-chloro-5-iodopyridin-4-yl)acetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Stage #1: 4-amino-3-chloro-5-iodopyridine With sodium hydride In tetrahydrofuran for 0.0833333h; Inert atmosphere;
Stage #2: acetyl chloride In tetrahydrofuran at 20℃; Inert atmosphere;
8-tert-butyl-4-chloro-6,7,8,9-tetrahydro-5H-pyrido[4,3-b]indole trifluoroacetate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
1%
Stage #1: 4-amino-3-chloro-5-iodopyridine; 4-tercbutyl-cyclohexanone With potassium <i>tert</i>-butylate; magnesium sulfate; acetic acid In N,N-dimethyl acetamide at 140℃; Inert atmosphere;
Stage #2: trifluoroacetic acid In water; acetonitrile
6
Example 6; 8-tert-Butyl-4-chloro-6,7,8,9-tetrahydro-5H-pyrido[4, 3-b]indoleA suspension of 3-chloro-4-amino-5-iodopyridine (2.0 g, 7.87 mmol), 4-tert- butylcyclohexanone (3.64 g, 23.6 mmol), potassium tert-butoxide (1 .148 g, 10.23 mmol), MgSO4 (0.474 g, 3.94 mmol) and acetic acid (0.708 g, 1 1 .8 mmol) in DMA (25 ml) was bubbled with N2 before Pd(OAc)2 (88 mg, 0.393 mmol) was added. The mixture was heated overnight at 140°C. The reaction mixture was partitioned with H2O/EtOAc (100 ml/100 ml). The aqueous phase was extracted with EtOAc (100 ml x 5). The combined organic phases were washed with brine, dried over Na2SO4 and concentrated. The residue was subjected to preparative HPLC (ds, eluting with CH3CN in H2O with 0.1 % TFA). The title compound was obtained as a TFA salt (38mg, 1 %).