Toluene → HCID 79290409, compound

HRID 1485469Notes

Reaction equation

HRID 1485469 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][C:12]([O:14]CC)=O.C1(C)C=CC=CC=1>C(OCC)(=O)C.C(O[Ti](OC(C)C)(OC(C)C)OC(C)C)(C)C>[F:8][C:7]1[C:2]2[NH:1][C:12](=[O:14])[CH2:11][CH2:10][NH:9][C:3]=2[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 1140TolueneHCID 61962718HCID 61962718, compound

Product 1

HCID 79290409HCID 79290409, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 178460666HCID 178460666, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A disposable tube was charged with ethyl 3-(2-amino-3-fluorophenylamino)propanoate (800 mg, 3.54 mmol) and a stirbar. Toluene (10 mL) was added, followed by tetraisopropoxytitanium (523 μl, 1.768 mmol), and the solution was stirred at 80° C. 0.5 h. The solution was diluted with ethyl acetate, concentrated with celite, and purified by silica gel chromatography (eluting with hexanes/ethyl acetate) to yield 9-fluoro-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one as a white amorphous solid (0.618 g, 3.43 mmol, 97%).

Workup

  1. custom0.5 h
  2. concentrationconcentrated with celite
  3. custompurified by silica gel chromatography (eluting with hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-af27866654c4474da16bffce2300f35e
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

Loading…