Potassium Phosphate, Tribasic → HCID 86699763, compound

HRID 515199Notes

Reaction equation

HRID 515199 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:23]([O-:25])=[O:24])=[C:5](OS(C(F)(F)F)(=O)=O)[CH:6]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:8]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:34](B1OC(C)(C)C(C)(C)O1)([CH3:36])=[CH2:35]>CN(C)C=O.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:34]([C:5]1[CH:6]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[N+:23]([O-:25])=[O:24])([CH3:36])=[CH2:35]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 86699764HCID 86699764, compound

Product 1

HCID 86699763HCID 86699763, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of trifluoro-methanesulfonic acid (3-methoxy-5-morpholin-4-yl-2-nitro-phenyl)ester (15.0 g, 38.7 mmol), potassium phosphate (24.6 g, 116 mmol) and 2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (8.4 g, 50.3 mmol) in dimethylformamide (80 ml) is degassed and flushed with argon for 20 min. To the reaction mixture is added 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (2.9 g, 3.9 mmol) and the resulting mixture is stirred at 120° C. for 16 h. After completion of the reaction (monitored by TLC), the mixture is diluted with water (50 ml) and extracted with ethyl acetate (3×70 ml). The combined organic layers are washed water (50 ml), brine (50 ml), dried over anhydrous sodium sulfate and evaporated in vacuo to get the crude product, which is purified by flash column chromatography (silica gel, 5% acetone/hexane) to yield 4-(3-isopropenyl-5-methoxy-4-nitro-phenyl)-morpholine (5.6 g, 20.0 mmol, 52%).

Workup

  1. customflushed with argon for 20 min
  2. customAfter completion of the reaction (monitored by TLC)
  3. extractionextracted with ethyl acetate (3×70 ml)
  4. washThe combined organic layers are washed water (50 ml), brine (50 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customto get the crude product, which
  8. customis purified by flash column chromatography (silica gel, 5% acetone/hexane)

Sources & evidence

ORD record
ord-2e4eb75859b24fb6a6951a09eb85da13
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

Loading…