2-Bromobenzonitrile → HCID 58996706, compound

HRID 1667533Notes

Reaction equation

HRID 1667533 reaction equation
[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+]>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]>[C:4]([O:3][C:1]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[C:18]#[N:19])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 162722-BromobenzonitrileHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 23676156Sodium t-butoxide

Product 1

HCID 58996706HCID 58996706, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of Boc-homopiperazine (900 mg, (4.63 mmol), 2-bromobenzonitrile (766 mg, 4.211 mmol), Pd2(dba)3 (193 mg, 0.21 mmol), xantphos (366 mg, 0.63 mmol), sodium t-butoxide (1.19 g, 12.6 mmol) in degassed anhydrous dioxane (10 mL) was heated at 120° C. in a sealed tube for 2 h. The mixture was allowed to cool and filtered through celite. The filtrate was concentrated and purified by chromatography (EtOAc/hexanes) to yield the title compound (905 mg, 71%). m/z (M+1) 301.27.

Workup

  1. temperatureto cool
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated
  4. custompurified by chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-c4e271d4ced64495baad2c7e508f3e6b
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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