3-Nitrophenylboronic Acid → HCID 56828549, compound

HRID 1696532Notes

Reaction equation

HRID 1696532 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[N+:9]([C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1)([O-:11])=[O:10]>>[N+:9]([C:12]1[CH:17]=[C:16]([C:2]2[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=2)[CH:15]=[CH:14][CH:13]=1)([O-:11])=[O:10]

Participants

3

Reactant 2

HCID 16773-Nitrophenylboronic AcidHCID 885792-Pyridinamine, 5-iodo-

Product 1

HCID 56828549HCID 56828549, compoundYield 60%

Procedure

Using the same procedureas for Example A43, 5-iodo-2-aminopyridine (0.31 g, 1.4 mmol) and 3-nitrophenylboronic acid (0.28 g, 1.7 mmol) were combined to yield 5-(3-nitrophenyl)pyridin-2-amine (0.18 g, 60%) as a white solid. 1H NMR (DMSO-d6): δ 8.37 (d, J=2.4 Hz, 1H), 8.34 (t, J=2.0 Hz, 1H), 8.11-8.04 (m, 2H), 7.83 (dd, J=8.0 Hz, 2.4 Hz, 1H), 7.68 (t, J=8.0 Hz, 1H), 6.55 (dd, J=8.4 Hz, 0.8 Hz, 1H), 6.26 (s, 2H); Exact mass: 215.0, Found: 216.0 (M+1)+.

Sources & evidence

ORD record
ord-f12ee80b436146f78e89fc5ec2fa35c8
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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