Triethylamine → HCID 59191237, compound

HRID 1023977Notes

Reaction equation

HRID 1023977 reaction equation
[F:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17]O)=[CH:11][C:10]=2[O:19][CH3:20])[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS([Cl:32])(=O)=O.[NH4+].[Cl-]>ClCCl>[Cl:32][CH2:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=2)=[C:10]([O:19][CH3:20])[CH:11]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 59191201HCID 59191201, compound

Product 1

HCID 59191237HCID 59191237, compoundYield 169.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{4-[(6-fluoropyridin-2-yl)oxy]-3-methoxyphenyl}prop-2-yn-ol (0.37 mmol; 102 mg) in dry dichloromethane (2 mL), under argon, cooled to −40° C., was added triethylamine (0.41 mmol; 56 μL) then methanesulfonyl chloride (0.39 mmol; 30 μL). The reaction mixture was allowed to stir for 6 hr, with gradual warming to room temperature. The reaction was hydrolysed with saturated NH4Cl, extracted with ethyl acetate. Combined organic phases were dried over Na2SO4, concentrated in vacuo. The title compound (185 mg; 47%) was obtained as a light oil, after purification on preparative TLC (cyclohexane/ethyl acetate: 7/3).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialCombined organic phases were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0fbfe1a6014644e2bffe463e3f7d394a
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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