(Diethylamino)sulfur trifluoride → HCID 119086490, compound

HRID 2202918Notes

Reaction equation

HRID 2202918 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:13])=[C:9]([CH2:11]O)[N:10]=2)[CH:7]=1.CCN(S(F)(F)[F:20])CC>C(Cl)Cl>[F:20][CH2:11][C:9]1[N:10]=[C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][N:6]2[C:8]=1[CH3:13]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 119086485HCID 119086485, compound

Product 1

HCID 119086490HCID 119086490, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (6-iodo-3-methylimidazo[1,2-a]pyridin-2-yl)methanol (600 mg) in DCM (2 ml) was added DAST (500 mg) at −78° C. The reaction mixture was then allowed slowly to warm up to room temperature, and stirred at the same temperature for 16 h. The reaction mixture was then diluted with DCM (100 ml), washed with saturated NaHCO3 solution (100 ml), and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM) to give the title compound (280 mg) as an off-white solid.

Workup

  1. washwashed with saturated NaHCO3 solution (100 ml)
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-aa17f20c6e6b428c9f0228e388f9d6cd
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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