4-Fluorophenyl isocyanate → HCID 11624639, compound

HRID 407432Notes

Reaction equation

HRID 407432 reaction equation
[F:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH2:16])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[CH:20][CH:19]=1>C(Cl)Cl>[F:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH:16][C:25]([NH:24][C:21]2[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=2)=[O:26])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 231394493-(4-fluoro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine

Product 1

HCID 11624639HCID 11624639, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-Fluoro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine (45 mg, 0.20 mmol) was dissolved in 3 mL of CH2Cl2, treated with 4-fluorophenylisocyanate (28 uL, 0.24 mmol), and stirred at room temperature overnight. The compound of interest precipitated out of solution and was filtered and washed with CH2Cl2 to afford Compound 31 as a white solid, 56 mg, 77% yield: LCMS m/z (%)=359 (M+H, 100). 1H NMR (400 MHz, acetone-d6) δ: 8.12 (s, 1H), 8.08 (s, 1H), 7.63 (ddd, J1=9.0 Hz, J2=2.6 Hz, 1H), 7.54 (m, 2H), 7.48 (d, J=2.8 Hz, 1H), 7.38 (d, JH,F=4.8 Hz, 1H), 7.13 (d, J=8.8 Hz, 1H), 7.05 (dd, J1=9.0 Hz, J2=9.0 Hz, 2H), 3.83 (s, 3H), 3.65 (s, 3H). 19F NMR (376 MHz, acetone-d6) δ: −123.08 (m, 1F), −177.41 (d, JH,F=5.3 Hz, 1F).

Workup

  1. customThe compound of interest precipitated out of solution
  2. filtrationwas filtered
  3. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-957a9a59fe374f9c9b432579a0f37b0f
Source dataset
uspto-grants-2014_06
Patent number
US08754238B2

Reaction notes

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