2-(Methylamino)ethanol → HCID 117892038, compound

HRID 930544Notes

Reaction equation

HRID 930544 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([F:14])[CH:6]=1)=[O:4].[CH3:15][CH2:16][N:17](C(C)C)[CH:18](C)C.CNCCO>ClCCl.O>[F:14][C:7]1[CH:6]=[C:5]([CH:3]2[O:4][CH2:15][CH2:16][N:17]([CH3:18])[CH2:2]2)[CH:10]=[CH:9][C:8]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 81531DiisopropylethylamineHCID 92133512HCID 92133512, compound

Product 1

HCID 117892038HCID 117892038, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

2-bromo-1-(3-fluoro-4-nitrophenyl)ethan-1-one E-1.17′″ (2.00 g; 7.63 mmol) is dissolved in dichloromethane (20 ml). DIPEA (1.4 ml; 8.00 mmol) and N-methyl ethanolamine (0.60 ml; 7.63 mmol) are added. The reaction mixture is stirred at 25° C. overnight. The reaction mixture is diluted with dichloromethane and water is added. The organic layer is separated and is dried with sodium sulfate and the solvent is removed under reduced pressure. The crude intermediate is dissolved in TFA (20 ml) and triethyl silane (8 mL) is added at 25° C. and then the reaction mixture is refluxed for 16 h. The reaction mixture is diluted with dichloromethane and the mixture is basified with saturated sodium hydrogencarbonate solution. The organic layer is separated and is dried with sodium sulfate and the solvent is removed under reduced pressure. The crude product is purified using normal phase chromatography (dichloromethane/methanol: 99:1).

Workup

  1. additionis added
  2. customThe organic layer is separated
  3. dry with materialis dried with sodium sulfate
  4. customthe solvent is removed under reduced pressure
  5. dissolutionThe crude intermediate is dissolved in TFA (20 ml)
  6. additiontriethyl silane (8 mL) is added at 25° C.
  7. temperaturethe reaction mixture is refluxed for 16 h
  8. additionThe reaction mixture is diluted with dichloromethane
  9. customThe organic layer is separated
  10. dry with materialis dried with sodium sulfate
  11. customthe solvent is removed under reduced pressure
  12. customThe crude product is purified

Sources & evidence

ORD record
ord-2964bcd2fb7a4016b7f74131f1801169
Source dataset
uspto-grants-2016_03
Patent number
US09296748B2

Reaction notes

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