Acetonitrile → HCID 178429691, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (±)-2-(hydroxy(7-methyl-5-(methylsulfonyl)-1-tosyl-1H-indol-4-yl)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile and (±)-2-(hydroxy(7-methyl-5-(methylsulfonyl)-1-tosyl-1H-indol-4-yl)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile (100 mg, 0.150 mmol) was added a 1 M solution of lithium tetrafluoroborate in MeCN (3.0 mL, 3 mmol). Water (0.3 mL) was then added and the reaction heated to 70° C. overnight. The reaction mixture was cooled to room temperature, diluted with water and extracted with EtOAc. The organic extract was dried over MgSO4, filtered and concentrated. The resulting residue was dissolved in EtOH (1.3 mL) and isomylamine (0.3 mL, 2.6 mmol) and KOH (0.072 g, 1.3 mmol) were added. The mixture was then heated to 100° C. for 1 h using microwave irradiation. The mixture was then concentrated directly and purified using FCC eluting with DCM:MeOH:NH4OH 100:0:0 to 80:18:2 to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 13.17 (br. s., 1H), 11.50 (br. s., 1H), 7.83-8.00 (m, 1H), 7.61-7.67 (m, 1H), 7.49-7.58 (m, 2H), 7.41-7.49 (m, 1H), 7.35 (q, J=2.40 Hz, 1H), 6.91 (dd, J=4.67, 7.58 Hz, 1H), 6.58 (dt, J=1.89, 3.66 Hz, 1H), 3.46 (m, 3H), 2.53 (s, 3H). HRMS calcd. for C19H16N4O3S (M+H)+ 381.1021. found 381.1013.

Provenance & Evidence