(Diethylamino)sulfur trifluoride → HCID 86729564, compound

HRID 2175400Notes

Reaction equation

HRID 2175400 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][CH:3]=1.CCN(S(F)(F)[F:16])CC>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][F:16])=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 64212496-Bromo-3-pyridinemethanol

Product 1

HCID 86729564HCID 86729564, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (6-bromopyridin-3-yl)methanol (1.00 g, 5.32 mmol) in dichloromethane (25 mL) at 0° C. was added DAST (0.70 mL, 5.32 mmol) and the resulting solution was stirred at 0° C. for one hour. The mixture was washed with a saturated sodium bicarbonate solution and concentrated. Flash column separation using a 0-10% ethyl acetate/hexane gradient gave F-1 (0.37 g, 37%). LRMS (ES) (M+14)+: observed=190.0/192.0, calculated=190.0/192.0.

Workup

  1. washThe mixture was washed with a saturated sodium bicarbonate solution
  2. concentrationconcentrated
  3. customFlash column separation

Sources & evidence

ORD record
ord-8a4db1dac34846f9855540617ffcd058
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

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