4-Methoxybenzylamine → 1-isopropyl-N-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridin-6-amine

HRID 1778022Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][C:5]2[N:8]=[CH:9][N:10]([CH:11]([CH3:13])[CH3:12])[C:4]=2[CH:3]=1.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1.CC([O-])(C)C.[Na+].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>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:11]([N:10]1[C:4]2[CH:3]=[C:2]([NH:21][CH2:20][C:19]3[CH:22]=[CH:23][C:16]([O:15][CH3:14])=[CH:17][CH:18]=3)[N:7]=[CH:6][C:5]=2[N:8]=[CH:9]1)([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-bromo-1-isopropyl-1H-imidazo[4,5-c]pyridine (intermediate 256, 2.134 g, 8.80 mmol), 4-methoxybenzylamine (1.389 ml, 10.38 mmol), NaOt-Bu (1.308 g, 13.20 mmol), Pd(OAc)2 (0.14 g, 0.616 mmol) and Xantphos (0.367 g, 0.616 mmol) in toluene (90 ml) was evacuated and purged with argon (3×) and then heated to 100° C. After 17 h, the reaction mixture was quenched with H2O and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over

Workup

customwas evacuated
custompurged with argon (3×)
customthe reaction mixture was quenched with H2O
extractionextracted with EtOAc (3×)
washThe combined organic layers were washed with brine
customdried over

Sources & evidence

ORD record: ord-21124ef1873e45b0addb797ea6fc6009
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266883B2

Reaction notes

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