methyl 1-chloro-5H-pyrido[4,3-b]indole-4-carboxylate → 1-chloro-5H-pyrido[4,3-b]indole-4-carboxamide

HRID 1896517

Reaction equation

[Cl:1][C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[C:5]([C:15]([O:17]C)=O)=[CH:4][N:3]=1.[Li][NH2:20]>C1COCC1>[Cl:1][C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[C:5]([C:15]([NH2:20])=[O:17])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture containing methyl 1-chloro-5H-pyrido[4,3-b]indole-4-carboxylate and LiNH2 (prepared in situ from ammonia and n-BuLi; 1.0 M in THF; 3.5 equiv) in THF (0.09 M) was heated in a microwave reactor at 100° C. for 1 min in a sealed tube. The reaction mixture was cooled to room temperature and partitioned between EtOAc and saturated NaHCO3. After separation of the organic phase, the aqueous phase was extracted again with EtOAc, and the combined organic phases were washed with brine, dried over MgSO4 and filtered. After evaporation of the organic solvent, the residue was purified by flash chromatography (10-70% EtOAc in hexanes) to provide the title compound as a white solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
custompartitioned between EtOAc and saturated NaHCO3
customAfter separation of the organic phase
extractionthe aqueous phase was extracted again with EtOAc
washthe combined organic phases were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
customAfter evaporation of the organic solvent
customthe residue was purified by flash chromatography (10-70% EtOAc in hexanes)

Sources & evidence

ORD record: ord-3fac0b86374e4f22b38c2e6e188545ea
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518964B2

Linked notes

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