Aniline → HCID 66911220, compound

HRID 341364Notes

Reaction equation

HRID 341364 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1I.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>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].C1(C)C=CC=CC=1>[F:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 669112262-Fluoro-1-iodo-3-methoxybenzene

Product 1

HCID 66911220HCID 66911220, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In a reaction vial were placed aniline (0.200 g. 2.182 mmol); 2-fluoro-1-iodo-3-methoxybenzene (0.500 g., 1.984 mmol), Pd2(dba)3 (0.091 g. 0.099 mmol), BINAP (0.185 g, 0.298 mmol), NaOtBu (0.286 g. 2.98 mmol), and toluene (3 mL). The reaction was stirred at 80° C. overnight and quenched with water. The organic layer was separated and concentrated. The residue was purified by flash column chromatography to provide the title compound as a brown oil (0.313 g). LCMS m/z=218.4 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 3.82 (s, 3H), 6.73 (ddd, J=10.93, 8.15, 1.64 Hz, 1H), 6.88-7.05 (m, 3H), 7.15 (d, J=7.33 Hz, 2H), 7.25-7.31 (m, 2H), 7.80 (s, 1H).

Workup

  1. customquenched with water
  2. customThe organic layer was separated
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-4c24368ef7a84549833c58453c0c4ab2
Source dataset
uspto-grants-2014_11
Patent number
US08895776B2

Reaction notes

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