Cesium carbonate → HCID 59216385, compound

HRID 2069812Notes

Reaction equation

HRID 2069812 reaction equation
[CH3:1][C:2]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[NH:11][CH2:10][CH2:9]2)([CH3:5])[C:3]#[N:4].[Br:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22](Br)[C:19]=1[CH:20]=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+]>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].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>[Br:17][C:18]1[C:19]([CH:20]=[O:21])=[C:22]([N:11]2[CH2:10][CH2:9][C:8]3[C:13](=[CH:14][CH:15]=[C:6]([C:2]([CH3:1])([CH3:5])[C:3]#[N:4])[CH:7]=3)[C:12]2=[O:16])[CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 126486412,6-DibromobenzaldehydeHCID 59216518HCID 59216518, compound

Product 1

HCID 59216385HCID 59216385, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalyst

Conditions

Temperature
110 °C

Procedure

To 1.3 g (6.07 mmol) 2-methyl-2-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-propionitrile dissolved in 20 ml degassed dioxane was added 6.40 g (24.27 mmol) 2,6-dibromobenzaldehyde, 3.96 g (12.14 mmol) cesium carbonate, 70 mg (0.121 mmol) Pd(dba)2, and 105 mg (0.182 mmol) xantphos. The mixture was heated to 110° C. for 3 h, cooled to room temperature, and filtered over Celite rinsing with dioxane. The mixture was then concentrated and purified by column chromatography, eluting with ethyl acetate/hexanes to provide 1.10 g (46%) 2-[2-(3-bromo-2-formylphenyl)-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl]-2-methylpropionitrile.

Workup

  1. customdegassed dioxane
  2. temperaturecooled to room temperature
  3. filtrationfiltered over Celite
  4. washrinsing with dioxane
  5. concentrationThe mixture was then concentrated
  6. custompurified by column chromatography
  7. washeluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c3cc7621eb764393b7b5409b964deb9d
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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