(5-Fluoro-1H-pyrrolo[2,3-b]pyridin-4-yl)methanol → 1H-Pyrrolo[2,3-b]pyridine-4-carboxaldehyde, 5-fluoro-

HRID 1968253Notes

Reaction equation

[F:1][C:2]1[C:3]([CH2:11][OH:12])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1>C1COCC1.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:7]=[N:6][C:5]2[NH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[CH:11]=[O:12]

Participants

Conditions

Temperature: 60 °C

Procedure

To a 250 mL round bottom flask equipped with a stirring bar was added (5-fluoro-1H-pyrrolo[2,3-b]pyridin-4-yl)methanol (2.01 g, 12.10 mmol) in THF (100 mL) under nitrogen. Manganese dioxide (10.52 g, 121 mmol) was added and the reaction mixture was stirred at 60° C. for 2 h. The organics were filtered through a pad of Celite, rinsed with EtOAc (100 mL) and concentrated. The resulting solid was triturated with EtOAc (50 mL) and filtered to give the title compound as a light yellow solid (1.3 g, 65.5%). 1H NMR (400 MHz, CD3OD) δ 4.59 (s, 1 H) 5.34 (d, J=3.54 Hz, 1 H) 5.86-6.08 (m, 1 H) 6.58 (d, J=3.28 Hz, 1 H). [M+H] calc'd for C8H5FN2O, 165; found, 165.5.

Workup

customTo a 250 mL round bottom flask equipped with a stirring bar
filtrationThe organics were filtered through a pad of Celite
washrinsed with EtOAc (100 mL)
concentrationconcentrated
customThe resulting solid was triturated with EtOAc (50 mL)
filtrationfiltered

Sources & evidence

ORD record: ord-00c7436b331d4eeeb663f874db805045
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420816B2

Reaction notes

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