Dimethylamine → HCID 67007525, compound

HRID 564010Notes

Reaction equation

HRID 564010 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:8][CH:9]([CH3:13])[C:10]([NH2:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.CNC.[C:17]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)([OH:19])=[O:18].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1(P([Pd](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:10]([CH:9]([S:8][C:4]1[CH:3]=[C:2]([C:23]2[CH:24]=[CH:25][C:20]([C:17]([OH:19])=[O:18])=[CH:21][CH:22]=2)[CH:7]=[CH:6][CH:5]=1)[CH3:13])(=[O:11])[NH2:12]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 62901447HCID 62901447, compound

Product 1

HCID 67007525HCID 67007525, compound

Reagents, catalysts & solvents 3

HCID 178420554HCID 178420554, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

1.0 g 2 (3-Bromo-phenoxy)-ethyl]-dimethyl-amine, 0.694 g of 4-carboxy-benzeneboronic acid, and 2.86 g potassium carbonate were stirred in a mixture of 5 ml dioxane and 5 ml water. 0.478 g tetrakis-triphenylphosphino-palladium were added under nitrogen atmosphere and the mixture was heated 85 C for 14 hrs. The mixture was diluted with 15 ml water and filtered. The filtrate was adjusted to pH 2 with conc. HCl and the precipitated product isolated by filtration.

Workup

  1. temperaturethe mixture was heated 85 C for 14 hrs
  2. filtrationfiltered
  3. customthe precipitated product isolated by filtration

Sources & evidence

ORD record
ord-64ed0f6cd4d143548d9682e3613f40d4
Source dataset
uspto-grants-2011_11
Patent number
US08067599B2

Reaction notes

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