4-Fluoroaniline → HCID 25111283, compound

HRID 2266964Notes

Reaction equation

HRID 2266964 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](CS([O-])(=O)=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[F:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CC(O)(C)C>[F:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 11430Potassium CarbonateHCID 86633818HCID 86633818, compound

Product 1

HCID 25111283HCID 25111283, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
110 °C

Procedure

Following general procedure A, a mixture of 3,4,5-trimethoxyphenylmethanesulfonate (131 mg, 0.5 mmol), 4-fluoroaniline (57 μL, 0.6 mmol), K2CO3 (97 mg, 0.7 mmol), 10 (4 mg, 1 mol %), 1 (2.5 mg, 1 mol %), and t-BuOH (6 mL) was heated to 110° C. for 16 h. The crude product was purified via the Biotage SP4 (silica-packed 25+M; 5-40% EtOAc/hexanes) to provide the title compound as a yellow oil (120 mg, 87%). 1H NMR (300 MHz, CDCl3) δ: 6.99 (m, 4H), 6.22 (s, 2H), 5.57 (s, 1H), 3.80 (s, 3H), 3.78 (s, 6H) ppm. 13C NMR (75 MHz, CDCl3) δ: 159.7, 156.5, 154.1, 140.5, 139.6, 132.5, 120.4, 120.3, 116.4, 116.1, 95.2, 61.3, 56.2 ppm. IR (neat, cm−1): 3360, 2937, 1597, 1499, 1454, 1216, 1129, 1007, 785. Anal. Calcd. for C15H16FNO3: C, 64.97; H, 5.82. Found: C, 65.24; H, 6.00.

Workup

  1. customThe crude product was purified via the Biotage SP4 (silica-packed 25+M; 5-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d378deb61c65472bb09021b93dd83426
Source dataset
uspto-grants-2010_12
Patent number
US07858784B2

Reaction notes

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