Pyridine → 2-(2-Chloro-4-cyano-5-methoxyphenyl)ethyl methanesulfonate

HRID 1186996Notes

Reaction equation

HRID 1186996 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[C:5]([O:10][CH3:11])=[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]=[C:5]([O:10][CH3:11])[C:6]([C:8]#[N:9])=[CH:7][C:2]=1[Cl:1])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 666440092-(2-Chloro-4-cyano-5-methoxyphenyl)ethanol

Product 1

HCID 866473062-(2-Chloro-4-cyano-5-methoxyphenyl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(2-chloro-4-cyano-5-methoxyphenyl)ethanol (205 mg, 0.969 mmol) DIPEA (0.846 mL, 4.84 mmol) and pyridine (0.0780 mL, 0.969 mmol) in DCM (3 mL) was treated dropwise with mesyl chloride (0.110 mL, 1.42 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. Purification of the residue by flash chromatography (20-50% ethyl acetate/hexanes) afforded the title intermediate. 1H-NMR (500 MHz, CDCl3) δ ppm 2.99 (s, 3H), 3.24 (t, J=6.6 Hz, 2H), 3.95 (s, 3H), 4.49 (t, J=6.6 Hz, 2H), 6.962 (s, 1H), 7.563 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-7e56c3097295436bac7cf197935a44a6
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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