Tetrabutylammonium Fluoride → HCID 59536452, compound

HRID 446924Notes

Reaction equation

Br[C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[N:8]([CH3:11])[N:9]=[CH:10][C:3]=12.C[Si]([C:16]#[C:17][C:18]1[CH:19]=[C:20]([NH:24][C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=[CH:22][CH:23]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:11][N:8]1[C:4]2=[CH:5][N:6]=[CH:7][C:2]([C:16]#[C:17][C:18]3[CH:19]=[C:20]([NH:24][C:25](=[O:32])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:21]=[CH:22][CH:23]=3)=[C:3]2[CH:10]=[N:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

In an adaption of GP 3c, 60 mg of 4-bromo-1-methyl-1H-pyrazolo[3,4-c]pyridine (Intermediate 2.1, 0.28 mmol, 1 eq), 140 mg N-(3-trimethylsilanylethynyl-phenyl)-benzamide (0.48 mmol, 1.68 eq.), 10 mg dichlorobis(triphenylphosphine)palladium (II) (PdCl2(PPh3)2) (0.014 mmol, 5 mol %) and 10.8 mg copper (I) iodide (0.057 mmol, 0.2 eq.) were dissolved in 1.4 mL THF (0.2 M) and treated with 0.35 mL tetra-n-butylammonium fluoride solution (1.0 M in THF, 0.35 mmol, 1.25 eq.). The resulting mixture was heated to 80° C. in a Biotage Initiator microwave oven for 30 min. Extractive work-up followed by column chromatography and preparative HPLC purification provided the target compound.

Workup

customExtractive work-up followed by column chromatography and preparative HPLC purification
customprovided the target compound

Sources & evidence

ORD record: ord-4356746b20724ab586c8f0354645e551
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481539B2

Reaction notes

Loading…