Water → HCID 66836095, compound

HRID 2404438Notes

Reaction equation

HRID 2404438 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14](Br)[CH:13]=1)[OH:11].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].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.C1(C)C=CC=CC=1.C(O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:12]1[CH:13]=[C:14]([C:24]2[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)[CH:15]=[CH:16][CH:17]=1)[OH:11]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 66835980HCID 66835980, compound

Product 1

HCID 66836095HCID 66836095, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of benzothiazol-2-yl(3-bromophenyl)methanol (200 mg), 4-methoxy-phenylboronic acid (142 mg), tetrakis(triphenylphosphine)palladium (50 mg), potassium carbonate (259 mg), water (4 mL), ethanol (1 mL) and toluene (9 mL) is purged with argon and refluxed for one night. After cooling at room temperature, the mixture is diluted with water and diethylether. The organic phase is dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography (heptane/ethyl acetate 2/1) to afford benzothiazol-2-yl(4′-methoxybiphenyl-3-yl)methanol as a beige solid.

Workup

  1. customis purged with argon
  2. temperaturerefluxed for one night
  3. additionthe mixture is diluted with water and diethylether
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by column chromatography (heptane/ethyl acetate 2/1)

Sources & evidence

ORD record
ord-dd9287847ca64eb2beb9df4c0e097409
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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