Toluene → methyl N-[(3'-cyanobiphenyl-4-yl)sulfonyl]valinate

HRID 606508

Reaction equation

HRID 606508 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:20]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)#[N:21].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>CCO.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:20]([C:22]1[CH:27]=[C:26]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH:25]=[CH:24][CH:23]=1)#[N:21]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 47337186methyl N-[(4-bromophenyl)sulfonyl]-L-valinate

Product 1

HCID 66769160methyl N-[(3'-cyanobiphenyl-4-yl)sulfonyl]valinateYield 97%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of methyl N-[(4-bromophenyl)sulfonyl]valinate obtained in Reference Example 92 (5.00 g, 14.3 mmol), (3-cyanophenyl)boronic acid (2.52 g, 17.1 mmol), tetrakis(triphenylphosphine)palladium (0.330 g, 0.286 mmol) and 2N aqueous sodium carbonate solution (8.57 mL, 17.1 mmol) in EtOH (15 mL)-toluene (50 mL) was heated under reflux for 8 hr under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was crystallized from hexane-ethyl acetate to give the title compound as a yellow powder (5.18 g, 97%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hr under nitrogen atmosphere
  3. washwashed with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-8b03e056be9b4eecb0cb5a8f50d27b6a
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Linked notes

Loading…