3-Chloroaniline → HCID 67378353, compound

HRID 1752511Notes

Reaction equation

HRID 1752511 reaction equation
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[Cl:58][C:59]1[CH:60]=[C:61]([CH:63]=[CH:64][CH:65]=1)[NH2:62]>O1CCOCC1.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].CCOC(C)=O.O>[Cl:58][C:59]1[CH:60]=[C:61]([NH:62][C:2]2[C:6]3=[N:7][CH:8]=[CH:9][CH:10]=[C:5]3[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:3]=2)[CH:63]=[CH:64][CH:65]=1

Participants

8

Reactant 4

HCID 79323-ChloroanilineHCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67378333HCID 67378333, compound

Product 1

HCID 67378353HCID 67378353, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3 (505 mg, 1.7 mmol), Cs2CO3 (1.1 g, 3.4 mmol), Pd2(dba)3 (119 mg, 0.13 mmol) and 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos) in a 50 mL round-bottomed flask were subjected to evacuation and purging (3× with Argon). A solution of 3-chloroaniline (0.20 mL, 1.87 mmol) in 1,4-dioxane (0.1 M) was added. The r×n mixture was heated to 100° C. After 12 h, the r×n was added to EtOAc:H2O (1:1; 250 mL) and the organic layer was separated. The aqueous layer was reextracted with EtOAc (2×50 mL). The collected organic layers were washed with brine (50 mL), dried (MgSO4), filtered and concentrated to afford a crude solid. The material was taken through to the next step.

Workup

  1. custompurging (3× with Argon)
  2. customthe organic layer was separated
  3. washThe collected organic layers were washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a crude solid

Sources & evidence

ORD record
ord-104c1d07117b4908af6a0907b0d74711
Source dataset
uspto-grants-2015_10
Patent number
US09163015B2

Reaction notes

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