3-Nitroaniline → HCID 58337727, compound

HRID 1887447Notes

Reaction equation

HRID 1887447 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].Cl[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.C(Cl)Cl.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 74233-NitroanilineHCID 10796Cesium carbonateHCID 122873-ChloropyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 58337727HCID 58337727, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

3-nitroaniline (1.82 g, 13.2 mmol, 1.5 eq), 3-chloropyridine (1 g, 8.8 mmol, 1 eq), Cs2CO3 (4.02 g, 12.3 mmol, 1.4 eq), Pd2(dba)3 (403 mg, 0.44 mmol, 0.05 eq) and Xantphos (511 mg, 0.88 mmol, 0.1 eq) were dissolved in toluene (10 mL) in a flame-dried sealed tube and heated at 110° C. for 18 h. The reaction was cooled to rt, diluted with CH2Cl2 and filtered through a plug of celite. Purification by flash chromatography on silica gel afforded 1.55 g (82%) of the title compound as an orange solid: 1H NMR (400 MHz, DMSO-d6) δ 8.89 (s, 1H), 8.42 (d, J=2.7 Hz, 1H), 8.17 (d, J=4.5, 1H), 7.79 (t, J=2.1 Hz, 1H), 7.64 (d, J=7.7 Hz, 1H), 7.59 (d, J=8.4 Hz, 1H), 7.52-7.45 (m, 2H), 7.33 (dd, J=8.2, 4.6 Hz, 1H); ES-MS [M+1]+: 216.1.

Workup

  1. customsealed tube
  2. temperatureThe reaction was cooled to rt
  3. filtrationfiltered through a plug of celite
  4. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-c8179b5d07df48178f58f156b607a09d
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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