Diethylamine → HCID 18398694, compound

HRID 1018956Notes

Reaction equation

HRID 1018956 reaction equation
I[C:2]1[CH:3]=[C:4]([P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])[CH:5]=[CH:6][CH:7]=1.[CH3:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(CC)CC>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.CCOC(C)=O.C(O)CC>[CH2:10]([O:9][P:8]([C:4]1[CH:3]=[C:2]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:16])[CH:22]=2)[CH:7]=[CH:6][CH:5]=1)([O:12][CH2:13][CH3:14])=[O:15])[CH3:11]

Participants

10

Reactant 4

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 27339503-Tolylboronic acidHCID 18374549HCID 18374549, compound

Product 1

HCID 18398694HCID 18398694, compound

Reagents, catalysts & solvents 5

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×HCID 10311-PropanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a compound of Step 1 (0.200 g, 0.588 mmol) in toluene (5 mL)—H2O (1.5 mL)-n-propanol (5 mL) were added 3-methyl phenyl boronic acid (0.158 g, 1.17 mmol), tris(dibenzylidene acetone)dipalladium (0.030 g), triphenylphosphine (0.123 g) and Et2NH (0.083 mL). After a period of 18 h at 80° C., the reaction mixture was partionned between EtOAc and H2O. The organic phase was separated, dried over Na2SO4, filtered and evaporated under reduced pressure. The title compound was obtained after flash chromatography (0.122 g).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-445568db763d4789a45a7a03f80d4f17
Source dataset
uspto-grants-2002_11
Patent number
US06486141B2

Reaction notes

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