Benzene, 1-bromo-3-nitro- → HCID 57942920, compound

HRID 1438105Notes

Reaction equation

HRID 1438105 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1B(O)O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:16]([C:19]1[CH:20]=[C:21](Br)[CH:22]=[CH:23][CH:24]=1)([O-:18])=[O:17]>COCCOC.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>[N+:16]([C:19]1[CH:24]=[C:23]([C:9]2[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:12]=[CH:11][CH:10]=2)[CH:22]=[CH:21][CH:20]=1)([O-:18])=[O:17]

Participants

6

Reactant 2

HCID 11457Benzene, 1-bromo-3-nitro-HCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid

Product 1

HCID 57942920HCID 57942920, compoundYield 76.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3A (1.46 g, 6.9 mmol) and 3-nitrobromobenzene (0.81 g, 4.0 mmol) in DME (40 mL) and 2.0 M Na2CO3 (8.0 mL) was degassed by bubbling argon for 5 min. To this solution, Pd(PPh3)4 (280 mg, 0.25 mmol) was added. The mixture was heated at 90° C. for 5 h. After cooling to rt, it was extracted with EtOAc and dried over Na2SO4. The product was purified by silica gel chromatography (CH2Cl2/hexanes=1/5) to give 4A (880 mg, 75% yield) as viscous oil. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.37 (s, 9H) 6.28 (t, J=3.52 Hz, 1H) 6.33 (dd, J=3.52, 1.76 Hz, 1H) 7.41 (dd, J=3.52, 1.76 Hz, 1H) 7.59 (m, 1H) 7.73 (d, J=7.91 Hz, 1H) 8.16 (m, 2H).

Workup

  1. customwas degassed
  2. customby bubbling argon for 5 min
  3. temperatureAfter cooling to rt
  4. extractionit was extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. customThe product was purified by silica gel chromatography (CH2Cl2/hexanes=1/5)

Sources & evidence

ORD record
ord-1fc8eb0dbef2420ba32eea31984c233c
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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