Dimethylformamide → HCID 18446964, compound

HRID 1268924Notes

Reaction equation

HRID 1268924 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:15][CH:14]=3)[O:10][N:9]=2)=[C:4]([CH3:23])[CH:3]=1.[CH3:24][N:25](C=O)C>[C-]#N.[Zn+2].[C-]#N.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>[CH3:21][CH:20]([CH3:22])[CH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:24]#[N:25])=[CH:3][C:4]=3[CH3:23])[N:12]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 18446945HCID 18446945, compound

Product 1

HCID 18446964HCID 18446964, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

A solution of 2.3 g (6.2 mmol) of 3-(4-bromo-2-methylphenyl)-5-(4-(2-methylpropyl)phenyl)-1,2,4-oxadiazole (from Step A), 1.46 g (12.4 mmol) of zinc cyanide and 2.15 g (1.86 mmol) of Pd(PPh3)4 in 20 mL of DMF was stirred at 100° C. for 20 h. The reaction was cooled and quenched with 10 mL of sat'd NaHCO3. The quenched mixture was extracted with 100 mL of dichloromethane. The extract was dried and concentrated to afford 1.40 g of the title compound which was used without further purification: ESI-MS 318 (M+H); LC-1: 4.8 min.

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with 10 mL of sat'd NaHCO3
  3. extractionThe quenched mixture was extracted with 100 mL of dichloromethane
  4. customThe extract was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-072eac94bb1e4178b6be364ca26686ad
Source dataset
uspto-grants-2007_04
Patent number
US07199142B2

Reaction notes

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