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Potassium Carbonate → 7-Hydroxy-2,4-diphenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

HRID 642281
Notes
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Reaction equation

HRID 642281 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10](Br)[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 866173544-Bromo-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 684280397-Hydroxy-2,4-diphenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl esterYield 36.7%

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-bromo-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (81 mg, 0.21 mmol), phenylboronic acid (34 mg, 0.28 mmol), tetrakis(triphenylphosphine)palladium(0)(25 mg, 0.02 mmol) and potassium carbonate (89 mg, 0.64 mmol) in dioxane (3 mL) and water (12 μL) was refluxed for 22 h before it was cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane to give the title compound as a white solid (29 mg): 1H NMR (CDCl3, 200 MHz): δ=11.46 (s, 1H), 8.49 (m, 2H), 8.14 (m, 2H), 7.53 (m, 6H), 4.56 (q, J=7.0 Hz, 2H), 1.54 (t, J=7.0 Hz, 3H).

Workup

  1. temperaturewas refluxed for 22 h before it
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane

Sources & evidence

ORD record
ord-b99074f3a1c348e6b0151de10752b432
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07696223B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes