3-{3-[2-(Pyridin-2-yl)ethenyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}phenol → 3-[3-(2-pyridin-2-yl-ethyl)-1H-pyrrolo[2,3-b]pyridine-5-yl]-phenol

HRID 729830Notes

Reaction equation

HRID 729830 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:8][C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=3)[CH:16]=2)[NH:11][CH:10]=1>[Pd].CO.C(Cl)Cl.CN(C=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=3)[CH:16]=2)[NH:11][CH:10]=1

Participants

4

Reactant 1

HCID 670612563-{3-[2-(Pyridin-2-yl)ethenyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}phenol

Product 1

HCID 597001333-[3-(2-pyridin-2-yl-ethyl)-1H-pyrrolo[2,3-b]pyridine-5-yl]-phenolYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 86602994MeOH DCM DMFSolvent

Procedure

A suspension of 3-[3-(2-pyridin-2-yl-vinyl)-1H-pyrrolo [2,3-b]pyridine-5-yl]-phenol (10 mg, 0.032 mmol) and 10 wt % Pd/C (1.7 mg, 0.0016 mmol) in 0.9 ml of a (1:1:1) mixture of MeOH/CH2Cl2/DMF was stirred for 2 days under H2 atmosphere. The mixture was adsorbed directly on silica gel. Purification on silica gel with a gradient of MeOH/CH2Cl2 afforded 3-[3-(2-pyridin-2-yl-ethyl)-1H-pyrrolo[2,3-b]pyridine-5-yl]-phenol as a yellow solid (6 mg, 60% yield). 1H NMR (500 MHz, DMSO-d6) δ 3.22 (t, J=7.5 Hz, 2H), 3.37 (t, J=7.5 Hz, 2H), 6.77 (d, J=7.5 Hz, 1H), 7.07 (s, 1H), 7.11 (d, J=7.0 Hz, 1H), 7.27 (m, 2H), 7.82 (m, 1H), 7.93 (d, J=7.0 Hz, 1H), 8.21 (s, 1H), 8.43 (m, 2H), 8.79 (d, J=5.5 Hz, 1H), 9.54 (broad s, 1H), 11.53 (s, 1H). MS: m/z 316 (M+H+).

Workup

  1. customPurification on silica gel with a gradient of MeOH/CH2Cl2

Sources & evidence

ORD record
ord-c8530eed4291462993e72553ebeb7a25
Source dataset
uspto-grants-2009_09
Patent number
US07582637B2

Reaction notes

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