Phenyl isocyanate → (3-Bromo-6-fluoro-pyridin-2-ylmethyl)-(4-methoxy-benzyl)-3-phenyl-urea

HRID 1749092Notes

Reaction equation

HRID 1749092 reaction equation
[Br:1][C:2]1[C:3]([CH2:9][NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[N:4][C:5]([F:8])=[CH:6][CH:7]=1.C(N(CC)C(C)C)(C)C.[C:29]1([N:35]=[C:36]=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>ClCCl>[Br:1][C:2]1[C:3]([CH2:9][N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:36]([NH:35][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:37])=[N:4][C:5]([F:8])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 81531DiisopropylethylamineHCID 70981253(3-Bromo-6-fluoro-pyridin-2-ylmethyl)-(4-methoxy-benzyl)-amine

Product 1

HCID 70981131(3-Bromo-6-fluoro-pyridin-2-ylmethyl)-(4-methoxy-benzyl)-3-phenyl-ureaYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3-bromo-6-fluoro-pyridin-2-ylmethyl)-(4-methoxy-benzyl)-amine (637 mg, 2.0 mmol, 1.0 equiv) and N,N-diisopropylethylamine (700 μL, 4.0 mmol, 2.0 equiv) in dichloromethane (10 mL) was added phenyl isocyanate (260 μL, 2.4 mmol, 1.2 equiv) and the reaction mixture was stirred at ambient temperature for 2 h. The reaction mixture was diluted with dichloromethane, washed with H2O, dried (MgSO4), filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-60%) to afford (1-(3-bromo-6-fluoro-pyridin-2-ylmethyl)-1-(4-methoxy-benzyl)-3-phenyl-urea (760 mg). MS: [M+H]+=445.

Workup

  1. washwashed with H2O
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-60%)

Sources & evidence

ORD record
ord-f30e23f9d9aa40d09cf747a9d5a6444c
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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