Sodium Bicarbonate → HCID 58387910, compound

HRID 2080022Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:14]=[CH:13][S:12][C:8]2=[N:9][C:10]=1N)=[O:4].N([O-])=[O:16].[Na+].C(=O)(O)[O-].[Na+]>[PH2](=O)O>[CH3:1][O:2][C:3]([C:5]1[C:10](=[O:16])[NH:9][C:8]2[S:12][CH:13]=[CH:14][C:7]=2[CH:6]=1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

6-Amino-thieno[2,3-b]pyridine-5-carboxylic acid methyl ester described in Preparation Example T-7 (10 mg, 48 μmol) and sodium nitrite (10 mg, 144 μmol) were dissolved in phosphinic acid (0.5 mL), and the solution was stirred at 0° C. for 1 hour. An aqueous solution of saturated sodium bicarbonate was added to the reaction solution at 0° C., which was then extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1), and the title compound (10 mg, 48 μmol, quantitatively) was obtained as a white solid.

Workup

extractionwhich was then extracted with ethyl acetate
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
customThe solvent was evaporated in vacuo
customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-b00ea1c8dadc49da8a223d9030dbe601
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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