Ethanol → HCID 86599796, compound

HRID 1374793Notes

Reaction equation

HRID 1374793 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]([CH3:15])=[C:5]2[S:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[CH2:39](O)[CH3:40]>C1(C)C=CC=CC=1.O.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>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([S:16][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:3]=3)[N:7]([CH2:11][C:12]([O:14][CH2:39][CH3:40])=[O:13])[C:6]=2[CH3:15])=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 10047206HCID 10047206, compound

Product 1

HCID 86599796HCID 86599796, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of the product of example 25 part (ii) (0.5 g) in ethanol (0.8 ml) and toluene (3 ml) was added 2M sodium carbonate solution in water (1.4 ml), phenylboronic acid (0.131 g) and tetrakis(triphenylphosphine)palladium(0) (1.2 g). The reaction was heated to reflux for 2 hours, cooled and concentrated in vacuo. The residue was purified by flash column chromatography to give the subtitle compound (0.4 g). This was used in step (ii) without further characterisation.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-5008cc425bb44a0babcc2cdb0276e3bd
Source dataset
uspto-grants-2007_01
Patent number
US07166607B2

Reaction notes

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