Triethylamine → Methanesulfonic acid 3-(6-(4-fluorophenyl)pyridin-3-yl)propyl ester

HRID 1896699Notes

Reaction equation

HRID 1896699 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][OH:22])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.C(OC(=O)CCC1C=NC(Br)=CC=1)C.FC1C=CC(B(O)O)=CC=1.C(N(CC)CC)C>C(Cl)Cl>[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][O:22][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2856454-Fluorophenylboronic acidHCID 691059353-[6-(4-Fluorophenyl)pyridin-3-yl]propan-1-olHCID 86251977Ethyl 3-(6-bromopyridin-3-yl)propanoate

Product 1

HCID 86621524Methanesulfonic acid 3-(6-(4-fluorophenyl)pyridin-3-yl)propyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

544.8 mg (4.75 mmol) of methanesulfonyl chloride were added dropwise with cooling to 1000 mg (4.32 mmol) of 3-(6-(4-fluorophenyl)pyridin-3-yl)propan-1-ol (prepared analogously to example 1a), starting from 3-(6-bromopyridin-3-yl)propionic acid ethyl ester and 4-fluorophenylboronic acid) and 656.3 mg (6.48 mmol) of triethylamine in 50 ml of methylene chloride. After 5 h at room temperature, the mixture was extracted with water, and the organic phase was separated and concentrated. Yield: 1.3 g (97%).

Workup

  1. customprepared analogously to example 1a),
  2. extractionthe mixture was extracted with water
  3. customthe organic phase was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1362052ab046458e8c377897fb3d14fd
Source dataset
uspto-grants-2013_08
Patent number
US08518976B2

Reaction notes

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