Toluene → HCID 72557543, compound

HRID 2220215Notes

Reaction equation

HRID 2220215 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]([C:25](=[O:27])[CH3:26])[CH2:7][C:8]3[CH:15]=[C:14](B4OC(C)(C)C(C)(C)O4)[CH:13]=[CH:12][C:9]=3[CH:10]=[CH:11][C:4]=2[CH:3]=1.[CH3:30][O:31][C:32](=[O:49])[C:33]1[CH:38]=[C:37]([CH:39]=[O:40])[CH:36]=[CH:35][C:34]=1OS(C(F)(F)F)(=O)=O.C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.CCO>[CH3:30][O:31][C:32](=[O:49])[C:33]1[CH:38]=[C:37]([CH:39]=[O:40])[CH:36]=[CH:35][C:34]=1[C:14]1[CH:13]=[CH:12][C:9]2[CH:10]=[CH:11][C:4]3[CH:3]=[C:2]([Cl:1])[CH:29]=[CH:28][C:5]=3[N:6]([C:25](=[O:27])[CH3:26])[CH2:7][C:8]=2[CH:15]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 15466849Methyl 5-formyl-2-(trifluoromethylsulfonyloxy)benzoateHCID 691963841-[2-Chloro-8-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-6H-dibenzo[b,f]azocin-5-yl]-ethanone

Product 1

HCID 72557543HCID 72557543, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A 15 mL three necked oven dried round bottom flask was cooled under argon and charged with Example 21A (50 mg, 0.12 mmol), Example 236A (47 mg, 0.15 mmol) and toluene (2 mL)/EtOH (1 mL). The mixture was purged with argon for 30 minutes. Pd(PPh3)4 (14 mg, 0.012 mmol) and 2 M Na2CO3 (187 μl, 0.36 mmol were added and the reaction was heated at 75° C. for 2 hours. The resulting mixture was poured into water (10 mL) and extracted with EtOAc (3×10 mL). The combined extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by radial chromatography (2 mm plate, 30% to 50% EtOAc/Hexanes) to give the desired product Example 236B (29 mg, 55%).

Workup

  1. dry with materialA 15 mL three necked oven dried round bottom flask
  2. temperaturewas cooled under argon
  3. customThe mixture was purged with argon for 30 minutes
  4. extractionextracted with EtOAc (3×10 mL)
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by radial chromatography (2 mm plate, 30% to 50% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-290f2b23488041d693d366ceead89b0b
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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