2-Aminopyridine → HCID 46830614, compound

HRID 473611Notes

Reaction equation

COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.CC([O-])(C)C.[Na+].[N:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[NH2:42].Cl[C:44]1[CH:63]=[CH:62][C:47]([O:48][C:49]2[C:54]([C:55]3[CH:60]=[CH:59][N:58]=[C:57]([CH3:61])[CH:56]=3)=[CH:53][CH:52]=[CH:51][N:50]=2)=[CH:46][CH:45]=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:61][C:57]1[CH:56]=[C:55]([C:54]2[C:49]([O:48][C:47]3[CH:62]=[CH:63][C:44]([NH:42][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][N:36]=4)=[CH:45][CH:46]=3)=[N:50][CH:51]=[CH:52][CH:53]=2)[CH:60]=[CH:59][N:58]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a sealed tube, under nitrogen, was added Pd2(dba)3 (0.19 g, 0.21 mmol), S-phos (0.36 g, 0.84 mmol), sodium 2-methylpropan-2-olate (2.0 g, 21 mmol), pyridin-2-amine (0.95 g, 10 mmol), 2-(4-chlorophenoxy)-3-(2-methylpyridin-4-yl)pyridine (2.5 g, 8.4 mmol), and toluene (18 mL). Reaction mixture was heated to 100° C. overnight. The reaction mixture was directly purified by silica gel chromatography (0-100% EtOAc/hexane). Solid precipitate formed upon rotovap of rich cut. The solid was collected and rinsed with EtOAc to afford N-(4-(3-(2-methylpyridin-4-yl)pyridin-2-yloxy)phenyl)pyridin-2-amine. MS (ESI, pos. ion) m/z: 355.1 (M+1). IC50 (uM) 0.003343.

Workup

customReaction mixture
customThe reaction mixture was directly purified by silica gel chromatography (0-100% EtOAc/hexane)
customSolid precipitate formed upon rotovap
customThe solid was collected
washrinsed with EtOAc

Sources & evidence

ORD record: ord-6ebf352fdc4c45c2a4b673ae25d31dce
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637500B2

Reaction notes

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