3,5-Dichloroaniline → HCID 85469492, compound

HRID 1048860Notes

Reaction equation

HRID 1048860 reaction equation
Br[C:2]1[O:3][C:4]([CH3:7])=[N:5][N:6]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+].[Cl:60][C:61]1[CH:62]=[C:63]([CH:65]=[C:66]([Cl:68])[CH:67]=1)[NH2:64]>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.[Pd].[Pd].C1(C)C=CC=CC=1>[Cl:60][C:61]1[CH:62]=[C:63]([NH:64][C:2]2[O:3][C:4]([CH3:7])=[N:5][N:6]=2)[CH:65]=[C:66]([Cl:68])[CH:67]=1

Participants

7

Reactant 4

HCID 122813,5-DichloroanilineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 252195362-Bromo-5-methyl-1,3,4-oxadiazole

Product 1

HCID 85469492HCID 85469492, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

In a 5 mL microwave tube, 2-bromo-5-methyl-1,3,4-oxadiazole (200 mg, 1.23 mmol, Eq: 0.05), Tris(dibenzylideneacetone)dipalladium(0) (56.2 mg, 61.4 μmol, Eq: 0.05) and (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (38.2 mg, 61.4 μmol, Eq: 0.05) were combined with toluene (10.0 ml) to give a brown suspension. Sodium tert-butoxide (236 mg, 2.45 mmol, Eq: 2.00) and 3,5-dichloroaniline (199 mg, 1.23 mmol, Eq: 1.00) were added. The solution was degassed with argon for 5 min, heated to 140° C. for 30 min under microwave.

Workup

  1. customto give a brown suspension
  2. customThe solution was degassed with argon for 5 min

Sources & evidence

ORD record
ord-6fe18935e3cc483986b4fa83923e8de2
Source dataset
uspto-grants-2016_07
Patent number
US09382218B2

Reaction notes

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