4-Aminopyridine → 3-(1H-Indol-4-YL)-5-(pyridin-4-ylamino)-phenol

HRID 1784816Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:18][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[CH:5]=[C:6]([O:8]CC2C=CC(OC)=CC=2)[CH:7]=1.N[C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1.Br[C:33]1[CH:38]=C(OCC2C=CC(OC)=CC=2)C=C(Br)[CH:34]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+]>O1CCOCC1>[NH:29]1[C:28]2[C:26](=[C:34]([C:2]3[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([NH:18][C:19]4[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=4)[CH:3]=3)[CH:33]=[CH:38][CH:27]=2)[CH:31]=[CH:30]1

Participants

Conditions

Temperature: 110 °C

Procedure

[3-Bromo-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-4-yl-amine. A solution of 4-aminopyridine (71 mg, 0.75 mmol), 1,3-dibromo-5-(4-methoxybenzyloxy)benzene (372.0 mg, 1.0 mmol), XantPhos (56 mg, 0.1 mmol), (dibenzylideneacetone)dipalladium (46 mg, 0.05 mmol), and sodium tert-butoxide (192 mg, 2.0 mmol) in dioxane (3 mL) was flushed with nitrogen and the reaction tube was sealed. The reaction mixture was heated to 110° C. for 16 h. After cooling, the reaction mixture was filtered through a short pad of Celite®, and the filtrate was concentrated. The residue was purified by silica gel column chromatography using 5% MeOH in methylene chloride to give a major fraction as a desired product which crystallized from a mixed solution of MeOH/methylene chloride. The crystals were filtered and washed with methanol to give 115 mg of pure 3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-4-yl-amine.

Workup

customthe reaction tube was sealed
temperatureAfter cooling
filtrationthe reaction mixture was filtered through a short pad of Celite®
concentrationthe filtrate was concentrated
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-da9dd3df01f34036a31335f47bc8e43d
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504401B2

Reaction notes

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