Hexane → HCID 59486219, compound

HRID 1949174Notes

Reaction equation

HRID 1949174 reaction equation
[CH2:1]([S:3][C:4]1[C:13]([C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24]C)=[O:15])=[C:12]([CH3:26])[C:11]2[C:6](=[CH:7][C:8]([C:27]([F:30])([F:29])[F:28])=[CH:9][CH:10]=2)[N:5]=1)[CH3:2].B(Br)(Br)Br.CCCCCC>C(Cl)Cl.O>[CH2:1]([S:3][C:4]1[C:13]([C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[OH:24])=[O:15])=[C:12]([CH3:26])[C:11]2[C:6](=[CH:7][C:8]([C:27]([F:30])([F:28])[F:29])=[CH:9][CH:10]=2)[N:5]=1)[CH3:2]

Participants

6

Reactant 3

HCID 8058HexaneHCID 25134Boron tribromideHCID 46911444HCID 46911444, compound

Product 1

HCID 59486219HCID 59486219, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 350 mg (0.8 mmol) 2-ethylsulfanyl-N-[(2-methoxyphenyl)-methyl]-4-methyl-7-(trifluoromethyl)-quinoline-3-carboxamide (example 84) in DCM (10 ml) was cooled to 0° C. 500 μl (4.9 mmol) boron tribromide were added dropwise at this temperature. The mixture was then stirred for 90 min at room temperature. Then it was diluted with water and extracted with DCM. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 4:1) of the residue yielded 240 mg (0.57 mmol, 70%) 2-ethylsulfanyl-N-[(2-hydroxyphenyl)-methyl]-4-methyl-7-(trifluoromethyl)-quinoline-3-carboxamide. MS: m/z 421.1 [M+H]+.

Workup

  1. extractionextracted with DCM
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-b64e05687bc740649de92d06ff36e8a4
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

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