4-Fluoroaniline → HCID 24808518, compound

HRID 1662285Notes

Reaction equation

HRID 1662285 reaction equation
[CH3:1][C:2]1[C:10]([NH:11][C:12](=[O:18])[CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:9]([CH3:19])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=O.[F:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1.[B][B][B][B][B][B][B][B][B][B]>CO>[F:21][C:22]1[CH:28]=[CH:27][C:25]([NH:26][CH:6]2[C:7]3[C:3](=[C:2]([CH3:1])[C:10]([NH:11][C:12](=[O:18])[CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:9]([CH3:19])[CH:8]=3)[CH2:4][CH2:5]2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 59808877HCID 59808877, compoundHCID 178419135HCID 178419135, compound

Product 1

HCID 24808518HCID 24808518, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(4,6-dimethyl-1-oxo-indan-5-yl)-3,3-dimethyl-butyramide (5 g, 19 mmol), 4-fluoroaniline (5 g, 45 mmol), and decaborane (4.5 g, 36.8 mmol) in 100 ml of anhydrous methanol was stirred for 2 days at room temperature in an high pressure reaction equipment. The reaction mixture was poured into 500 ml of ice-water with strong stirring and the precipitates were filtered and washed with water. The dried solid was crystallized from hexane/ethyl acetate (5:1) to give white crystals (6 g, 86%). 1H-NMR δ (DMSO-d6, 400 MHz): 9.08 (brs, 1H, exchangeable with D2O, NH), 6.98 (s, 1H), 6.92 (t, J=8.8 Hz, 2H), 6.69 (dd, J=4.8 and 8.8 Hz, 2H), 5.76 (d, J=8.0 Hz, 1H, exchangeable with D2O, NH), 4.86 (q, J=8.0 Hz, 1H), 2.86 (ddd, J=4.8, 8.7 and 16.2 Hz, 1H), 2.70 (quint, J=8.1 Hz, 1H), 2.46 (m, 1H), 2.22 (s, 2H), 2.11 (s, 3H), 2.06 (s, 3H), 1.74 (m, 1H), 1.07 (s, 9H). MS: 369 (M+1).

Workup

  1. stirringwith strong stirring
  2. filtrationthe precipitates were filtered
  3. washwashed with water
  4. customThe dried solid was crystallized from hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-8250b5cc0b2d43979ebe4e908bfb1ff0
Source dataset
uspto-grants-2011_10
Patent number
US08030518B2

Reaction notes

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