Tetrabutylammonium Fluoride → HCID 58266582, compound

HRID 1505954Notes

Reaction equation

[Cl:1][C:2]1[CH:24]=[N:23][C:5]2[N:6](COCC[Si](C)(C)C)[C:7]3[CH:12]=[N:11][C:10]([C:13]#[N:14])=[CH:9][C:8]=3[C:4]=2[CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:1][C:2]1[CH:24]=[N:23][C:5]2[NH:6][C:7]3[CH:12]=[N:11][C:10]([C:13]#[N:14])=[CH:9][C:8]=3[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 3-chloro-9-(2-trimethylsilanylethoxymethyl)-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (24.2 mg, 67.4 μmol) in THF (1.3 mL) was treated with TBAF (398 μL, 1.35 mmol) and heated to 60° C. for 2 h. The reaction mixture was cooled to ambient temperature and the solvent removed in vacuo. The resultant residue was dissolved in DCM/EtOAc, absorbed onto silica gel, and purified by flash chromatography (silica, 4 g column, Biotage, 1-20% methanol in DCM containing 0 1% 7N ammonia in MeOH). Collecting appropriate fractions afforded a solid which was further purified by preparative HPLC (5-85% MeCN in water (0.1% NH4OH) over 30 min, 35 mL/min) to afford the title compound as an off-white solid (10 mg, 66%). 1H NMR (400 MHz, DMSO-D6): 13.07 (s, 1H), 9.05 (d, J=0.9 Hz, 1H), 8.95 (d, J 2.4 Hz, 1H), 8.92 (d, J=0.9 Hz, 1H), 8.73 (d, J=2.4 Hz, 1H). LCMS (Method E): RT=3.98 min, M+H+=229.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
customthe solvent removed in vacuo
dissolutionThe resultant residue was dissolved in DCM/EtOAc
customabsorbed onto silica gel
custompurified by flash chromatography (silica, 4 g column, Biotage, 1-20% methanol in DCM containing 0 1% 7N ammonia in MeOH)
customCollecting appropriate fractions
customafforded a solid which
customwas further purified by preparative HPLC (5-85% MeCN in water (0.1% NH4OH) over 30 min, 35 mL/min)

Sources & evidence

ORD record: ord-e283db7f5a20467eb27657ff48e989d8
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216980B2

Reaction notes

Loading…