Sodium Carbonate → HCID 86587977, compound

HRID 1797161Notes

Reaction equation

HRID 1797161 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:22])[CH:11]([C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)[CH2:12][CH:13]=[CH2:14])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:23]([C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1)#[N:24].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.O.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>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:22])[CH:11]([C:15]2[CH:20]=[CH:19][C:18]([C:29]3[CH:28]=[CH:27][CH:26]=[C:25]([C:23]#[N:24])[CH:30]=3)=[CH:17][CH:16]=2)[CH2:12][CH:13]=[CH2:14])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 86587978HCID 86587978, compound

Product 1

HCID 86587977HCID 86587977, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
90 °C

Procedure

To an Argon-purged solution of 2-(4-bromophenyl)-pent-4-enoic acid (3,5-dichloro-phenyl)-amide (1.5 g, 3.7 mmol) in toluene/EtOH (2:1 v/v, 30 mL) was added 3-cyanophenylboronic acid (0.99 g, 6.7 mmol, 1.8 eq), Pd(PPh3)4 (160 mg, 0.44 mmol, 12%), and a solution of Na2CO3 (2.12 g, 20 mmol, 5.4 eq) in 10 mL of water. The reaction mixture was heated at 90° C. for 16 h. The mixture was partitioned between EtOAc (50 mL) and 10% NaHCO3 (50 mL) and the organic phase separated. The organic phase was washed with 10% NaHCO3 (30 mL) and saturated brine (30 mL), dried (Na2SO4), and concentrated. Chromatography on silica gel (20% EtOAc/hexanes) gave 2-(3′-cyano-biphenyl-4-yl)-pent-4-enoic acid (3,5-dichloro-phenyl)-amide as a yellow oil (685 mg, 44%). 1H NMR (300 MHz, CD3OD): δ 7.93 (m, 2H), 7.81 (m, 2H), 7.66 (m, 4H), 7.49 (m, 2H), 7.12 (t, 1H), 5.89 (m, 1H), 5.21 (m, 2H), 3.76 (t, 1H), 3.11 (m, 1H), 2.73 (m, 1H).

Workup

  1. customThe mixture was partitioned between EtOAc (50 mL) and 10% NaHCO3 (50 mL)
  2. customthe organic phase separated
  3. washThe organic phase was washed with 10% NaHCO3 (30 mL) and saturated brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7cab8722cc6d481595f5b55c8ef5e3d9
Source dataset
uspto-grants-2006_04
Patent number
US07034056B2

Reaction notes

Loading…