(Diethylamino)sulfur trifluoride → HCID 178434334, compound

HRID 2070919Notes

Reaction equation

Br[C:2]1[N:19]=[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([F:18])([F:17])[CH:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[N:4]2[N:3]=1.C([N:22](S(F)(F)F)[CH2:23][CH3:24])C>C(Cl)(Cl)Cl>[F:17][C:10]([F:18])([CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[C:9]1[N:4]2[N:3]=[C:2]([NH:19][C:5]3[CH:24]=[C:23]4[C:8]([C:9]([CH3:10])=[N:4][NH:22]4)=[CH:7][CH:6]=3)[N:19]=[C:5]2[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2-Bromo-5-(difluoro(tetrahydro-2H-pyran-4-yl)methyl)-[1,2,4]triazolo[1,5-a]pyridine. (Diethylamino)sulfur trifluoride (4.26 mL, 32.2 mmol) was added to a stirred solution of (2-bromo-[1,2,4]triazolo[1,5-c]pyridin-5-yl)(tetrahydro-2H-pyran-4-yl)methanone (2 g, 6.45 mmol) in chloroform (40 mL) in a high pressure flask under nitrogen. The flask was sealed and heated at 50° C. for 16 h. The reaction was quenched with methanol (1 mL). The resulting mixture was diluted with ethyl acetate (200 mL) and washed with saturated aqueous sodium bicarbonate. The organics were washed with brine and then dried over magnesium sulfate, filtered, and concentrated on a rotary evaporator. The residue was purified using flash chromatography (5-50% ethyl acetate in hexane), to give the desired product (1.7 g, 5.12 mmol, 79% yield) as a light yellow solid. MS (ESI) m/z 334.2 [M+2]+.

Workup

customThe flask was sealed
customThe reaction was quenched with methanol (1 mL)
additionThe resulting mixture was diluted with ethyl acetate (200 mL)
washwashed with saturated aqueous sodium bicarbonate
washThe organics were washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated on a rotary evaporator
customThe residue was purified

Sources & evidence

ORD record: ord-6be8264b7ec049feac43448e416867d3
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299056B2

Reaction notes

Loading…