Triethylsilane → 3-(5-Cyclopropyl-1,3,4-oxadiazol-2-yl)-5-(2,3-dihydro-1-methyl-1H-indol-5-yl)-2-pyridinamine

HRID 1053122Notes

Reaction equation

[CH:1]1([C:4]2[O:8][C:7]([C:9]3[C:10]([NH2:25])=[N:11][CH:12]=[C:13]([C:15]4[CH:16]=[C:17]5[C:21](=[CH:22][CH:23]=4)[N:20]([CH3:24])[CH:19]=[CH:18]5)[CH:14]=3)=[N:6][N:5]=2)[CH2:3][CH2:2]1.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O.O>[CH:1]1([C:4]2[O:8][C:7]([C:9]3[C:10]([NH2:25])=[N:11][CH:12]=[C:13]([C:15]4[CH:16]=[C:17]5[C:21](=[CH:22][CH:23]=4)[N:20]([CH3:24])[CH2:19][CH2:18]5)[CH:14]=3)=[N:6][N:5]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-(5-cyclopropyl-[1,3,4]oxadiazol-2-yl)-5-(1-methyl-1H-indol-5-yl)-pyridin-2-ylamine (160 mg, 0.48 mmol) in TFA at 0° C. was added triethylsilane (0.2 mL, 1.20 mmol) drop-wise over a period of 5 min, and stirred for 2 h at 0° C. The reaction mixture was diluted with water (20 mL) and neutralized with saturated aqueous NaHCO3 solution and extracted with ethyl acetate (3×20 mL). The organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to get crude product. The crude product was purified by column chromatography using 100-200 mesh silica gel and compound was eluted with 40% ethyl acetate in petroleum ether to afford the title compound.

Workup

extractionextracted with ethyl acetate (3×20 mL)
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulphate
concentrationconcentrated under reduced pressure
customto get crude product
customThe crude product was purified by column chromatography
washwas eluted with 40% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-73b31d1a120b469bae9fb0823fd6c88e
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09393248B1

Reaction notes

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