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Tetrapropylstannane → 7-Hydroxy-2-phenyl-4-propyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

HRID 642330
Notes
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Reaction equation

HRID 642330 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].[CH2:23]([Sn](CCC)(CCC)CCC)[CH2:24][CH3:25]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([CH2:23][CH2:24][CH3:25])[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 16585TetrapropylstannaneHCID 866173544-Bromo-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 684281827-Hydroxy-2-phenyl-4-propyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl esterYield 57.7%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalyst
HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-bromo-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (152 mg, 0.40 mmol), tetra-n-propyltin (211 μL, 0.80 mmol) and bis(triphenylphosphine)-palladium(II) dichloride (28 mg, 0.04 mmol) in dimethylformamide (2.5 mL) was stirred at 130° C. for 1 h before it was cooled to room temperature, quenched with water, filtered. The filtrate was 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 hexanes to give the title compound as a white solid (79 mg): MS: (+) m/z 343.00 (M+1), MS: (−) m/z 341.00 (M−1).

Workup

  1. temperaturewas cooled to room temperature
  2. customquenched with water
  3. filtrationfiltered
  4. customThe filtrate was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-2b2a00b5d8ac4b38b40fc448785c5e5b
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07696223B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes