Cesium fluoride → HCID 59518016, compound

HRID 1160797Notes

Reaction equation

HRID 1160797 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH2:12]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)[CH2:13][CH2:14][CH3:15].[F-].[Cs+]>O1CCOCC1>[CH2:12]([C:16]1[CH:21]=[CH:20][C:19]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=2)=[CH:18][CH:17]=1)[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 701324-Bromo-2-nitroanilineHCID 41008604-Butylphenylboronic acid

Product 1

HCID 59518016HCID 59518016, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A Smith Process Vial charged with 4-bromo-2-nitroaniline (205 mg, 0.945 mmol), 4-butyl phenyl boronic acid (336 mg, 1.89 mmol), cesium fluoride (430 mg, 2.83 mmol), bis(tri-t-butyl-phosphine)-palladium (24.1 mg, 0.0472 mmol), and dioxane (2 ml) is purged with Argon (g) for 5 minutes and then heated in a microwave to 120° C. for 15 minutes. The crude reaction is filtered through Celite using EtOAc as eluent. The filtrate is concentrated in vacuo and the crude product is purified with silica gel flash column chromatography (0-100% ethyl acetate in hexanes gradient) to afford 4′-butyl-3-nitro-biphenyl-4-ylamine: ESMS m/z 271.2 (M+H+).

Workup

  1. customis purged with Argon (g) for 5 minutes
  2. customThe crude reaction
  3. filtrationis filtered through Celite
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe crude product is purified with silica gel flash column chromatography (0-100% ethyl acetate in hexanes gradient)

Sources & evidence

ORD record
ord-176b8bbd9c3442dab95f46e75af4e7d9
Source dataset
uspto-grants-2010_10
Patent number
US07816542B2

Reaction notes

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