Toluene → HCID 86607516, compound

HRID 2368747Notes

Reaction equation

HRID 2368747 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[C:9]([OH:18])=[C:10]2[CH:17]=[CH:16][S:15][C:11]2=[C:12](O)[N:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4].O=P(Cl)(Cl)[Cl:21].C1(C)C=CC=CC=1.C([O-])(O)=O.[Na+]>CCOC(C)=O>[CH2:1]([O:5][C:6]([C:8]1[C:9]([OH:18])=[C:10]2[CH:17]=[CH:16][S:15][C:11]2=[C:12]([Cl:21])[N:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178450865HCID 178450865, compound

Product 1

HCID 86607516HCID 86607516, compoundYield 143.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4,7-dihydroxy-thieno[2,3-c]pyridine-5-carboxylic acid butyl ester (267 mg, 1 mmol), POCl3 (217 mg, 1.4 mmol), and toluene (4 ml) was heated in a microwave oven at 140° C. for 15 min. The same procedure was repeated with a second batch. Both batches were combined, conc. aqueous NaHCO3 (40 ml) and EtOAc (40 ml) were added and the mixture was stirred vigorously for 45 min. The organic layer was then separated, dried over MgSO4 and concentrated in vacuo to give a tan solid (410 mg). Purification by flash column chromatography on silica gel using CH2Cl2: EtOAc=9:1 as the eluent yielded the title compound as a tan solid (297 mg, first major fraction). MS-(−)-ion: M−1=284.3.

Workup

  1. customThe organic layer was then separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a969ee7773c4260ac90b41930705c99
Source dataset
uspto-grants-2014_04
Patent number
US08703795B2

Reaction notes

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