Bromobenzene → HCID 58504041, compound

HRID 2407778Notes

Reaction equation

HRID 2407778 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:24])[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.Br[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CC(C)([O-])C.[K+]>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].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[O:24]=[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 7961BromobenzeneHCID 23665647Potassium tert-butoxideHCID 58504081HCID 58504081, compound

Product 1

HCID 58504041HCID 58504041, compoundYield 55.7%

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
105 °C

Procedure

A flask was charged with the compound prepared in Example 302 (0.533 g), 1-bromobenzene (0.252 g), potassium tert-butoxide (0.252 g), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.056 mg), and bis(dibenzylideneacetone)palladium (0.037 g) and flushed with nitrogen gas. Toluene (30 mL) which was thoroughly purged with nitrogen gas was added and the reaction mixture heated at 105° C. for 18 hours. The reaction mixture was concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 10% ethyl acetate/hexane) to furnish the title compound (0.365 g) with the following physical properties.

Workup

  1. customflushed with nitrogen gas
  2. customToluene (30 mL) which was thoroughly purged with nitrogen gas
  3. additionwas added
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customto afford the crude material, which
  6. customwas purified by flash column chromatography (eluant: 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3430b6e2ba7242c6aaf06b97e227c218
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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