Triethylamine → Methyl 2-((1-(2-tert-butoxy-2-oxoethyl)-1H-indol-6-ylamino)methyl)-4-chloro-1-methyl-1H-indole-3-carboxylate

HRID 453856Notes

Reaction equation

Br[CH2:2][C:3]1[N:4]([CH3:17])[C:5]2[C:10]([C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[C:9]([Cl:16])[CH:8]=[CH:7][CH:6]=2.[NH2:18][C:19]1[CH:27]=[C:26]2[C:22]([CH:23]=[CH:24][N:25]2[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:21][CH:20]=1.C(N(CC)CC)C>C1C=CC=CC=1.C(OCC)(=O)C>[C:32]([O:31][C:29](=[O:30])[CH2:28][N:25]1[C:26]2[C:22](=[CH:21][CH:20]=[C:19]([NH:18][CH2:2][C:3]3[N:4]([CH3:17])[C:5]4[C:10]([C:11]=3[C:12]([O:14][CH3:15])=[O:13])=[C:9]([Cl:16])[CH:8]=[CH:7][CH:6]=4)[CH:27]=2)[CH:23]=[CH:24]1)([CH3:35])([CH3:33])[CH3:34]

Participants

Conditions

Temperature: 25 °C

Procedure

Methyl 2-(bromo-methyl)-4-chloro-1-methyl-1H-indole-3-carboxylate (1.10 mmol, 1.0 equiv.) and tert-butyl 2-(6-amino-1H-indol-1-yl)acetate (intermediate A) (1.10 mmol, 1.0 equiv.) were dissolved in benzene (5 ml) and triethylamine (1.3 mmol, 1.2 equiv.) and refluxed for 16 h. The reaction mixture was cooled to 25° C., diluted with ethyl acetate and washed with water and sat. NaCl solution. Drying over Na2SO4 was then carried out, followed by concentration under reduced pressure. The crude product was purified by column chromatography (40% ethyl acetate in hexane). Yield: 55%

Workup

washwashed with water and sat. NaCl solution
dry with materialDrying over Na2SO4
concentrationfollowed by concentration under reduced pressure
customThe crude product was purified by column chromatography (40% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-f1c1fff7fd3743aebba8912a66a5d9a6
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492559B2

Reaction notes

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