Tetrabutylammonium Fluoride → 3-(1-Methyl-1H-pyrazolo[3,4-c]pyridin-4-ylethynyl)-phenylamine

HRID 446921Notes

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]([NH2:24])[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]([NH2:24])[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, 639 mg of 4-bromo-1-methyl-1H-pyrazolo[3,4-c]pyridine (Intermediate 2.1, 3 mmol, 1 eq), 931 mg 3-trimethylsilanylethynyl-phenylamine (4.9 mmol, 1.6 eq.), 106 mg dichlorobis(triphenylphosphine)palladium (II) (PdCl2(PPh3)2) (0.15 mmol, 5 mol %) and 115 mg copper (I) iodide (0.6 mmol, 0.2 eq.) were dissolved in 15 mL THF (0.2 M) and treated with 3.6 mL tetra-n-butylammonium fluoride solution (1.0 M in THF, 3.6 mmol, 1.2 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 provided the target compound.

Workup

customprovided the target compound

Sources & evidence

ORD record: ord-fabc70b9f8ed4bc0b93a97bfbb1bca80
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481539B2

Reaction notes

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