Toluene → HCID 22107169, compound

HRID 1456828Notes

Reaction equation

HRID 1456828 reaction equation
C[C:2]1[C:3]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)C(Br)=[C:5]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1)[C:4]=2[C:23]1C=CC=CC=1.CB(O)O.C([O-])([O-])=O.[Na+].[Na+].[C:39]1([CH3:45])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>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>[CH3:23][C:4]1[C:3]2[C:2]([CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[C:45]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:5]=1[C:13]1[CH:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 139377Methylboronic AcidHCID 22107192HCID 22107192, compound

Product 1

HCID 22107169HCID 22107169, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a solution of methyl 1-bromo-2-(4-methylsulfonylphenyl)-3-phenylazulene (0.20 g) in toluene (10.0 ml) was added methylboronic acid (0.13 g), tetrakis(triphenylphosphine)palladium (0) (0.05 g) and 2M aqueous Na2CO3 (0.9 ml), and the reaction mixture was heated under reflux for 2 hr. The reaction mixture was poured into ice-water, followed by extracted with EtOAc. The combined EtOAc extracts were washed with water and brine, dried over Na2SO4, and concentrated. The crude product was purified by SiO2 column chromatography (benzenee/EtOAc, 20: 1) to give the title compound (0.15 g) as violet crystals; mp 165°-167° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 hr
  3. extractionby extracted with EtOAc
  4. washThe combined EtOAc extracts were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by SiO2 column chromatography (benzenee/EtOAc, 20: 1)

Sources & evidence

ORD record
ord-72e29df6d0364c52a85261e477f9a992
Source dataset
uspto-grants-1998_12
Patent number
US05843999

Reaction notes

Loading…