2-Bromo-5-fluorobenzonitrile → HCID 67416726, compound

HRID 1803623Notes

Reaction equation

HRID 1803623 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:15]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:16]=1[C:17]#[N:18].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:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:15]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:16]=2[C:17]#[N:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 936542-Bromo-5-fluorobenzonitrileHCID 143452tert-Butyl piperazine-1-carboxylateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxide

Product 1

HCID 67416726HCID 67416726, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
105 °C

Procedure

A mixture of piperazine-1-carboxylic acid tert-butyl ester (1.05 g, 5.65 mmol), 2-bromo-5-fluoro-benzonitrile (1.13 g, 5.65 mmol), Pd2(dba)3 (259 mg, 0.283 mmol), xanthphos (490 mg, 0.848 mmol), sodium tert-butoxide (1.63 g, 16.95 mmol) in anhydrous 1,4-dioxane (10 ml) was heated at 100-110° C. in a sealed tube for 1 h. After cooled to room temperature, the mixture was filtered through celite then concentrated before purified by chromatography (hexanes/EtOAc) to provide compound as indicated (1.31 g, 76%). m/z (M+1) 306.21.

Workup

  1. temperatureAfter cooled to room temperature
  2. filtrationthe mixture was filtered through celite
  3. concentrationthen concentrated
  4. custombefore purified by chromatography (hexanes/EtOAc)
  5. customto provide compound as indicated (1.31 g, 76%)

Sources & evidence

ORD record
ord-9a9661853a5048b5b8ad4be4cc37dd16
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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