6-(benzyloxy)pyridin-3-amine → 3-Bromo-5-((4-methoxybenzyl)oxy)aniline

HRID 1784811Notes

Reaction equation

C(OC1N=CC([NH:15][C:16]2[CH:21]=[C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[CH:19]=[C:18]([Br:32])[CH:17]=2)=CC=1)C1C=CC=CC=1.C(OC1N=CC(N)=CC=1)C1C=CC=CC=1.BrC1C=C(OCC2C=CC(OC)=CC=2)C=C(Br)C=1.CC([O-])(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[Br:32][C:18]1[CH:17]=[C:16]([NH2:15])[CH:21]=[C:20]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)[CH:19]=1

Participants

Conditions

Temperature: 120 °C

Procedure

(6-benzyloxy-pyridin-3-yl)-[3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-amine. A dry tube was charged with 6-benzyloxy-pyridin-3-ylamine (68 mg, 0.34 mmol), 1,3-dibromo-5-(4-methoxy-benzyloxy)-benzene (126 mg, 0.34 mmol), NaOtBu (46 mg, 0.48 mmol), Pd2(dba)3 (3.1 mg, 0.0034 mmol), BINAP (6.3 mg, 0.01 mmol) and degassed toluene (2 mL). The tube was heated in a microwave reactor at 120° C. for 1 h. After cooling down to room temperature, the reaction mixture was loaded directly on Celite®. Chromatographic purification afforded 6-benzyloxy-pyridin-3-yl)-[3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-amine as a yellow oil (78.8 mg, 47%).

Workup

customdegassed toluene (2 mL)
temperatureAfter cooling down to room temperature
customChromatographic purification

Sources & evidence

ORD record: ord-931461be7229496e836defd5785e4db4
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504401B2

Reaction notes

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