Isocyanate → HCID 10573917, compound

HRID 1603762Notes

Reaction equation

HRID 1603762 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](C(N=[N+]=[N-])=O)[CH:5]=[N:6][CH:7]=1.[N-:13]=[C:14]=[O:15].[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][C:26]=1[C:27]([F:30])([F:29])[F:28])[NH:23][CH2:22][CH2:21]2>C1(C)C=CC=CC=1.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([NH:13][C:14]([N:23]2[C:24]3[C:20](=[CH:19][C:18]([O:17][CH3:16])=[C:26]([C:27]([F:29])([F:30])[F:28])[CH:25]=3)[CH2:21][CH2:22]2)=[O:15])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 105034IsocyanateHCID 112067135-Methoxy-6-(trifluoromethyl)indolineHCID 156228505-Bromopyridine-3-carbonyl azide

Product 1

HCID 10573917HCID 10573917, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

5-Bromo-3-pyridylcarbonylazide (3.7 g, 16 mmoles) was heated under reflux in dry toluene (100 ml) for 1 hr. After cooling the resulting solution of isocyanate was treated with a solution of 5-methoxy-6-trifluoromethyl indoline (D11) (3.5 g, 16 mmoles) in dichloromethane (600 ml) and stirred overnight. The mixture was concentrated in vacuo and the residue triturated with diethyl ether. Filtration and washing with more diethyl ether gave the title compound (D26) (5.4 g, 81%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue triturated with diethyl ether
  3. filtrationFiltration
  4. washwashing with more diethyl ether

Sources & evidence

ORD record
ord-ea758860a31e454ba0a44fe7f2883def
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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