3-Fluorophenyl isocyanate → HCID 59813370, compound

HRID 1925350Notes

Reaction equation

HRID 1925350 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:25]=[C:24]2[C:19]([CH:20]=[CH:21][C:22]([NH2:26])=[CH:23]2)=[CH:18][CH:17]=1.[F:27][C:28]1[CH:29]=[C:30]([N:34]=[C:35]=[O:36])[CH:31]=[CH:32][CH:33]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:25]=[C:24]2[C:19]([CH:20]=[CH:21][C:22]([NH:26][C:35]([NH:34][C:30]3[CH:31]=[CH:32][CH:33]=[C:28]([F:27])[CH:29]=3)=[O:36])=[CH:23]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 1230643-Fluorophenyl isocyanateHCID 67520515HCID 67520515, compound

Product 1

HCID 59813370HCID 59813370, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(6,7-dimethoxyquinolin-4-yloxy)naphthalen-2-amine (0.158 g, 0.45 mmol) in 20 mL of THF was added 3-fluorophenyl isocyanate (0.057 mL, 0.50 mmol). The solution was stirred for 16 h at RT under an atmosphere of nitrogen. The reaction was concentrated and the crude solid was treated with CH2Cl2. The resulting solid was collected by vacuum filtration and dried in vacuo to afford the desired compound. MS (ESI, pos. ion) m/z: 484.0 (M+1). Mass Calc'd for C28H22FN3O4: 483.497.

Workup

  1. concentrationThe reaction was concentrated
  2. additionthe crude solid was treated with CH2Cl2
  3. filtrationThe resulting solid was collected by vacuum filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-42c9f11d2b274374905a9f000a31f41b
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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