Ethanol → HCID 58613354, compound

HRID 1244242Notes

Reaction equation

HRID 1244242 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([NH:19][S:20]([C:23]3[S:24][C:25](Br)=[CH:26][CH:27]=3)(=[O:22])=[O:21])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.[C:39]([O-])([O-])=[O:40].[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]=[C:16]([NH:19][S:20]([C:23]3[S:24][C:25]([C:33]4[CH:34]=[CH:35][C:30]([Cl:29])=[CH:31][CH:32]=4)=[CH:26][CH:27]=3)(=[O:22])=[O:21])[C:17]([O:40][CH3:39])=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 58613356HCID 58613356, compound

Product 1

HCID 58613354HCID 58613354, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of the bromo intermediate D5 (1.20 g, 0.0023 moles), 4-chlorophenylboronic acid (0.55 g, 0.0034 moles), K2CO3 (2M solution, 15 ml), ethanol (15 ml) and toluene (50 ml) at room temperature was degassed by bubbling argon through the solution for 10 minutes. Pd(PPh3)4 (0.4 g, 0.000375 moles) was added and the mixture heated at 60° C. under argon for 4 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 D7 as a white foam (1.09 g, 86%). M-H 547. 1H NMR: δ CDCl3 1.47 (9H, s) 2.83(4H, m), 3.50 (4H, m), 3.66 (3H,s), 6.55 (1H, s), 6.96 (1H, s), 7.12 (1H, d), 7.33–7.50 (5H, m).

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-5f5c52e70d274249ad675ecc74c80859
Source dataset
uspto-grants-2006_10
Patent number
US07122538B2

Reaction notes

Loading…