Ethyl orthoformate → HCID 178505977, compound

HRID 1848049Notes

Reaction equation

HRID 1848049 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH2:10](OC(OCC)OCC)C>C(O)=O>[F:1][C:2]1[CH:3]=[C:4]2[N:9]=[CH:10][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 222931555-Fluoro-2,3-pyridinediamine

Product 1

HCID 178505977HCID 178505977, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 5-fluoropyridine-2,3-diamine (1.13 g) from Step 1 of this Example, formic acid (0.5 mL), and triethylorthoformate (15 mL) was heated at 100° C. for 1 h. The reaction mixture was cooled to rt, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified via silica gel flash chromatography eluting with 100% DCM to 10% MeOH in DCM to afford 6-fluoro-3H-imidazo[4,5-b]pyridine (760 mg, 36% over two steps) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 13.09 (br s, 1H), 8.49 (s, 1H), 8.37 (s, 1H), 7.97 (d, J=7.9 Hz, 1H). LCMS (ESI) m/z 138 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified via silica gel flash chromatography
  5. washeluting with 100% DCM to 10% MeOH in DCM

Sources & evidence

ORD record
ord-4e4c39ae4afa4606a0f9cfe389f6d4bf
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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