Triethylamine → HCID 59191237, compound

HRID 626067Notes

Reaction equation

HRID 626067 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-af682eaf20c449f8acf19496f1ea7740
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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