Dimethylformamide → HCID 24993727, compound

HRID 1673239Notes

Reaction equation

HRID 1673239 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[O:14][C:15]([CH3:26])([CH3:25])[CH2:16][CH:17]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[C:11]3=[CH:10][C:9]=2[C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)=[C:4]([Cl:34])[CH:3]=1.[CH3:35][N:36](C=O)C>O.[C-]#N.[C-]#N.[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[Cl:34][C:4]1[CH:3]=[C:2]([C:35]#[N:36])[CH:7]=[CH:6][C:5]=1[C:8]1[N:13]=[C:12]2[O:14][C:15]([CH3:25])([CH3:26])[CH2:16][CH:17]([NH:18][C:19](=[O:24])[C:20]([CH3:22])([CH3:23])[CH3:21])[C:11]2=[CH:10][C:9]=1[C:27]1[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=1

Participants

7

Reactant 2

HCID 6228DimethylformamideHCID 67019901HCID 67019901, compound

Product 1

HCID 24993727HCID 24993727, compound

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)Catalyst

Conditions

Temperature
120 °C

Procedure

To a suspension of the product of Step A (141 mg, 0.25 mmol), Zn(CN)2 (29.4 mg, 0.25 mmol), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (5.2 mg, 0.005 mmol), and dppf (6.9 mg, 0.01 mmol) in 5.0 mL of DMF was added one drop of H2O. The solution was degassed and stirred at 120° C. for 16 h, the reaction mixture was cooled to rt and diluted with EtOAc (20 mL). The solid was filtered off and washed with EtOAc. The filtrate was concentrated and chromatography on a Biotage 40+M cartridge using 2:3 v/v EtOAc/hexanes as the eluant afforded the title compound: 1H NMR δ 1.27 (s, 9H), 1.48 (s, 3H), 1.56 (s, 3H), 1.84 (m, 1H), 2.26 (m, 1H), 5.50 (m, 1H), 5.82 (br. s, 1H), 6.95 (d, J=8.2, 2H), 7.19 (d, J=8.3, 2H), 7.41-7.58 (m, 4H).

Workup

  1. customThe solution was degassed
  2. temperaturethe reaction mixture was cooled to rt
  3. additiondiluted with EtOAc (20 mL)
  4. filtrationThe solid was filtered off
  5. washwashed with EtOAc
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2783e51eead1425fa5ca611eb9a86775
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

Loading…