Ethanol → HCID 69544987, compound

HRID 1244243Notes

Reaction equation

HRID 1244243 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[C:10]([NH:22][S:23]([C:26]2[S:27][C:28](Br)=[CH:29][CH:30]=2)(=[O:25])=[O:24])([N:19]([CH3:21])[CH3:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1.C([O-])([O-])=O.[K+].[K+].C(O)C>C1C=CC([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)=CC=1.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[C:10]([NH:22][S:23]([C:26]2[S:27][C:28]([C:36]3[CH:37]=[CH:38][C:33]([Cl:32])=[CH:34][CH:35]=3)=[CH:29][CH:30]=2)(=[O:25])=[O:24])([N:19]([CH3:21])[CH3:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 86603939HCID 86603939, compound

Product 1

HCID 69544987HCID 69544987, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of the bromo intermediate D6 (0.2 g, 0.00037 moles), 4-chlorophenylboronic acid (0.070 g, 0.00045 moles), K2CO3 (2M solution, 1 ml), ethanol (1 ml) and toluene (2 ml) at room temperature was degassed by bubbling argon through the solution for 10 minutes. Pd(PPh3)4 (0.1 g, 0.000086 moles) was added and the mixture heated at 60° C. under argon for 24 hours. Upon cooling the mixture was partitioned between water and ethyl acetate. The aqueous phase was re-extracted with ethyl acetate (×3) and the combined organic phase washed with water, brine then dried over anhydrous MgSO4. The solution was evaporated to dryness then purified by chromatography over silica eluting, with hexane up to 50% EtOAc/hexane, affording the title compound D8 as a off white foam, which was used directly in the next step. M-H 563.

Workup

  1. customby bubbling argon through the solution for 10 minutes
  2. temperatureUpon cooling the mixture
  3. customwas partitioned between water and ethyl acetate
  4. extractionThe aqueous phase was re-extracted with ethyl acetate (×3)
  5. washthe combined organic phase washed with water, brine
  6. dry with materialthen dried over anhydrous MgSO4
  7. customThe solution was evaporated to dryness
  8. customthen purified by chromatography over silica eluting, with hexane up to 50% EtOAc/hexane

Sources & evidence

ORD record
ord-7770a560554f4f98b445df49b9f7d8f9
Source dataset
uspto-grants-2006_10
Patent number
US07122538B2

Reaction notes

Loading…