3-Nitrophenylboronic Acid → Tert-butyl 4-(3-nitrophenyl)-1,2,3,6-tetrahydropyridine-1-carboxylate

HRID 2196573Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].FC(F)(F)S(O[C:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH:20]=1)(=O)=O.C(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N+:1]([C:4]1[CH:5]=[C:6]([C:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH:20]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-Nitrophenylboronic acid (1.00 g, 5.99 mmol), 172a (2.183 g, 6.59 mmol), Pd(dppf)2Cl2.CH2Cl2 (200 mg, 0.273 mmol) and K2CO3 (1.90 g, 13.8 mmol) was stirred under N2 and heated at 80° C. for 16 h. After the usual work-up the crude material was purified by flash chromatography using 15 to 20% EtOAc in hexane to afford 187 (1.31 g, 4.30 mmol, 72%). LRMS (ESI): calc. 304.1, found 327.2 (MNa)+.

Workup

customAfter the usual work-up the crude material was purified by flash chromatography

Sources & evidence

ORD record: ord-005c2b07e07344c9ad3b5186f52d9bbe
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338437B2

Reaction notes

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