HCID 178469171, compound → ethyl 1-(2,3-difluorobenzyl)-4-hydroxy-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 1912613Notes

Reaction equation

[F:1][C:2]1[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:20])=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:13]([OH:14])=[C:8]2[CH2:7][CH2:6]1>C1C=CC=CC=1.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:20])=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:13]([OH:14])=[C:8]2[CH:7]=[CH:6]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 1-(2,3-difluorobenzyl)-4-hydroxy-6-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (9.9 g, 27.0 mmol) in benzene (150 mL) was added manganese dioxide (13.81 g, 135 mmol) (activated 85%, 5 micron) and the mixture was heated to 80° C. under nitrogen atmosphere for 3.5 h. The mixture was filtered hot through celite washing with EtOAc (250 mL) and the filtrate was concentrated, dried in vacuo to provide ethyl 1-(2,3-difluorobenzyl)-4-hydroxy-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (9.0 g, 23.39 mmol, 87% yield) as greyish solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.47 (t, J=7.12 Hz, 3 H), 2.84 (s, 3 H), 4.47 (q, J=7.02 Hz, 2 H), 5.51 (s, 2 H), 6.64 (d, J=3.32 Hz, 1 H), 6.79-6.90 (m, 1 H), 6.92-7.03 (m, 2 H), 7.08 (q, J=8.32 Hz, 1 H), 12.78 (s, 1H); LCMS (m/z) ES+=347 (M+1).

Workup

filtrationThe mixture was filtered hot
washthrough celite washing with EtOAc (250 mL)
concentrationthe filtrate was concentrated
customdried in vacuo

Sources & evidence

ORD record: ord-52684a8f1d55473bb9e306a24802f0c4
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609653B2

Reaction notes

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