2-Bromobenzonitrile → HCID 67415713, compound

HRID 1667530Notes

Reaction equation

HRID 1667530 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][NH:12][CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[C:19]#[N:20].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[CH2:9][CH:10]2[CH:14]([CH2:13][N:12]([C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[C:19]#[N:20])[CH2:11]2)[CH2:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 162722-BromobenzonitrileHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylateHCID 23676156Sodium t-butoxide

Product 1

HCID 67415713HCID 67415713, compoundYield 74%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

A mixture of hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester (464 mg, (2.19 mmol), 2-bromobenzonitrile (400 mg, 2.19 mmol), Pd2(dba)3 (100 mg, 0.11 mmol), xantphos (190 mg, 0.33 mmol), sodium t-butoxide (618 mg, 6.57 mmol) in degassed anhydrous dioxane (10 mL) was heated at 120° C. in a sealed tube for 1 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 (505 mg, 74%). m/z (M+1) 313.41.

Workup

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

Sources & evidence

ORD record
ord-ec76302f8ce54078acda480d7c384800
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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