Dimethylformamide → Allyl-{5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pent-4-ynyl}-methyl-amine

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]#[C:18][CH2:19][CH2:20][CH2:21]OS(C)(=O)=O)=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[CH2:27]([CH2:30][NH2:31])[CH:28]=C.[CH3:32]N(C=O)C>>[CH2:30]([N:31]([CH2:21][CH2:20][CH2:19][C:18]#[C:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:9]=[CH:10]2)[CH3:32])[CH:27]=[CH2:28]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 4437323-Buten-1-amine

HCID 86585584Methanesulfonic acid 5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pent-4-ynyl ester

Product 1

HCID 18679475Allyl-{5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pent-4-ynyl}-methyl-amineYield 55%

Procedure

100 mg (0.26 mmol) Methanesulfonic acid 5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pent-4-ynyl ester and 0.5 ml (5.2 mmol) N-allylmethylamine were stirred in 1 ml DMF at 60° C. for 1.5 h. The solution was concentrated, and the residue was dissolved in water and CH2Cl2. 2M NaOH was added and the inorganic phase was extracted with CH2Cl2. The combined organic phases were washed with water and dried over Na2SO4. Column chromatography with CH2Cl2/MeOH 19:1 yielded 50 mg (55%) Allyl-{5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pent-4-ynyl}-methyl-amine as light yellow oil, MS: 347 (MH+).