Water → HCID 117760043, compound

HRID 709835Notes

Reaction equation

HRID 709835 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:15]([CH2:16][C:17]2([C:22]#[N:23])[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:14][C:13]([CH2:24]O)=[CH:12][N:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:46].O>C1(C)C=CC=CC=1>[Br:46][CH2:24][C:13]1[CH:14]=[C:15]([CH2:16][C:17]2([C:22]#[N:23])[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:10]([C:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=2[F:1])=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 117760218HCID 117760218, compound

Product 1

HCID 117760043HCID 117760043, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-((2-(2-fluoro-5-methoxyphenyl)-5-(hydroxymethyl)pyridin-3-yl)methyl)cyclopentanecarbonitrile (353 mg) and triphenylphosphine (410 mg) in toluene (10 mL) was added carbon tetrabromide (512 mg), and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (339 mg) as white crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a23c5b44012b4fa29c320b21cabc383a
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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