2-Bromobenzaldehyde → HCID 11218363, compound

HRID 598788Notes

Reaction equation

HRID 598788 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.Cl.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:2]3[C:3](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[N:20]2)=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 811292-BromobenzaldehydeHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 23676156Sodium t-butoxide

Product 1

HCID 11218363HCID 11218363, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromobenzaldehyde (74 mg, 0.4 mmol), 4-methoxyphenylhydrazine hydrochloride (70 mg, 0.4 mmol), sodium tert-butoxide (115 mg, 1.2 mmol), palladium(II) acetate (18 mg, 0.08 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (44 mg, 0.08 mmol) were dissolved in toluene (0.6 mL) and heated to 100° C. overnight. The mixture was filtered through Celite with ethyl acetate, and the filtrate was concentrated. SiO2 chromatography (5-20% ethyl acetate/hexanes) gave the desired product, 30 mg. LC-MS (C14H12N2O calculated 224) m/z 225 (M+H).

Workup

  1. filtrationThe mixture was filtered through Celite with ethyl acetate
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-8999b0a565294e1abadee7053f2803fb
Source dataset
uspto-grants-2011_03
Patent number
US07897634B2

Reaction notes

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