Pyridine → HCID 86647304, compound

HRID 1474250Notes

Reaction equation

HRID 1474250 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([C:10]#[N:11])[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][OH:14].N1C=CC=CC=1.[S:21](Cl)([CH3:24])(=[O:23])=[O:22]>C(Cl)Cl>[CH3:24][S:21]([O:14][CH2:13][CH2:12][C:3]1[CH:4]=[CH:5][C:6]([C:10]#[N:11])=[C:7]([O:8][CH3:9])[C:2]=1[Cl:1])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 66643840HCID 66643840, compound

Product 1

HCID 86647304HCID 86647304, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(2-chloro-4-cyano-3-methoxyphenyl)ethanol (205 mg, 0.969 mmol) DIPEA (0.846 mL, 4.84 mmol) and pyridine (0.078 mL, 0.969 mmol) in DCM (3 mL) was treated dropwise with mesyl chloride (0.110 mL, 1.417 mmol). The reaction was stirred for 2 hours and was then diluted with DCM and washed twice with aq. citric acid, then washed with brine, and dried over sodium sulfate. The residue was purified by flash chromatography (20-50% ethyl acetate/hexanes) to afford the title intermediate.

Workup

  1. washwashed twice with aq. citric acid
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe residue was purified by flash chromatography (20-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-85ee1bb2d3d84066845de933cfb0903c
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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