Propargyl bromide → HCID 137210843, compound

HRID 530185Notes

Reaction equation

HRID 530185 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:3]=1[NH:4][C:5]([O:7][CH3:8])=[O:6].[CH2:14](Br)[C:15]#[CH:16].CCN(C(C)C)C(C)C>CN(C=O)C.O>[F:1][C:2]1[C:3](=[CH:9][C:10](=[N:13][CH2:16][C:15]#[CH:14])[CH2:11][CH:12]=1)[NH:4][C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 81531DiisopropylethylamineHCID 28377672Methyl (5-amino-2-fluorophenyl)carbamate

Product 1

HCID 137210843HCID 137210843, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

under an atmosphere of nitrogen, compound methyl 2-fluoro-5-aminoaniline formate (72.5 mg, 0.39 mmol) was dissolved in dried DMF (5 mL), then propargyl bromide (44 μL, 0.59 mmol) and DIPEA (140 μL, 0.78 mmol) were added. The resulting solution was stirred for 6 h at 60° C., and diluted with water (10 mL) and extracted with EtOAc (10 mL×3). The combined organic phases were washed with saturated saline solution (15 mL×3), dried with anhydrous Na2SO4, concentrated and then loaded on chromatography column (PE/EtOAc=6:1-4:1) to produce a product of methyl 2-fluoro-5-(N-propargyl-imino)-aniline formate (70.1 mg, 81%);

Workup

  1. extractionextracted with EtOAc (10 mL×3)
  2. washThe combined organic phases were washed with saturated saline solution (15 mL×3)
  3. dry with materialdried with anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b82333ab43e44a76a5a0655bf2d635a9
Source dataset
uspto-grants-2016_05
Patent number
US09353048B2

Reaction notes

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