Triethylsilane → 3-(1-Isopropyl-1H-[1,2,3]triazol-4-yl)-5-(1-methyl-2,3-dihydro-1H-indol-5-yl)-pyridin-2-ylamine

HRID 1053128Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-(1-isopropyltriazol-4-yl)-5-(1-methylindol-5-yl)pyridin-2-amine (170 mg, 0.511 mmol) in TFA (5.0 mL) was added triethylsilane (0.16 mL, 1.022 mmol) at 0° C. The reaction temperature was stirred for 1 h at 0° C. The reaction mixture was poured into ice-cold water (20 mL), basified with saturated NaHCO3, extracted with EtOAc (30 mL), dried over anhydrous Na2SO4 and evaporated the solvent under reduced pressure to get crude compound. Crude compound was washed with diethyl ether to afford title compound as a yellow solid.

Workup

extractionextracted with EtOAc (30 mL)
dry with materialdried over anhydrous Na2SO4
customevaporated the solvent under reduced pressure
customto get crude compound
washCrude compound was washed with diethyl ether

Sources & evidence

ORD record: ord-a9fc7081e86647e8bf8baf43e32bbc4d
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09393248B1

Reaction notes

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