Acetic Acid → methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

HRID 1968170Notes

Reaction equation

HRID 1968170 reaction equation
[NH:1]1[C:5]2[N:6]=[CH:7][CH:8]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=[CH:2]1.C1N2CN3CN(C2)CN1C3.[C:24](O)(=[O:26])C>O>[CH:24]([C:3]1[C:4]2[C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=[N:6][C:5]=2[NH:1][CH:2]=1)=[O:26]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 22832048Methyl 1H-pyrrolo[2,3-b]pyridine-4-carboxylate

Product 1

HCID 53412886methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 1H-pyrrolo[2,3-b]pyridine-4-carboxylate (500 mg, 2.84 mmol) and hexamethylenetetramine (796 mg, 5.68 mmol) were combined in water (8 mL) and glacial acetic acid (16 mL) and heated at 100° C. overnight then cooled to room temperature. The reaction mixture was extracted with ethyl acetate and the organics were dried over MgSO4 and concentrated in vacuo to give a residue. Purification of the residue by silica gel chromatography (50% EtOAc/Hexanes) gave the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 10.07 (s, 1H), 8.57 (s, 1H), 8.48 (d, 1H, J=4.8 Hz), 7.48 (d, 1H, J=4.8 Hz), 5.74 (d, 1H, J=6.8 Hz), 3.91 (s, 3H), 2.78 (s, 3H). [M+H] found 205.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe organics were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give a residue
  5. customPurification of the residue by silica gel chromatography (50% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-8c11dde35c624ee5ac1f56cc2d653292
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

Loading…