Toluene → HCID 86607516, compound

HRID 1465962Notes

Reaction equation

HRID 1465962 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-a10c8f5bc7ac40fb96ac1695a2b7f4d6
Source dataset
uspto-grants-2015_04
Patent number
US09000006B2

Reaction notes

Loading…