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2-Amino-5-bromopyridine → benzyl (E)-3-(6-aminopyridin-3-yl)acrylate

HRID 18208
Notes
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Reaction equation

HRID 18208 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[C:9]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:12])[CH:10]=[CH2:11].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(C(C)C)CC)(C)C>C(#N)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[NH2:1][C:2]1[N:3]=[CH:4][C:5](/[CH:11]=[CH:10]/[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 706222-Amino-5-bromopyridineHCID 75617Benzyl acrylateHCID 80271Tri-o-tolylphosphineHCID 81531Diisopropylethylamine

Product 1

HCID 11128853benzyl (E)-3-(6-aminopyridin-3-yl)acrylateYield 39.3%

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 7854PropionitrileSolvent

Procedure

A solution of 2-amino-5-bromopyridine (2.25 g, 13.0 mmole), benzyl acrylate (3.2 g, 19.7 mmole), Pd(OAc)2 (0.31 g, 1.4 mmole), tri-ortho-tolylphosphine (0.73 g, 2.4 mmole), and diisopropylethylamine (3.5 mL, 20.0 mmole) in propionitrile (50 mL) was heated at reflux overnight. The dark mixture was filtered through Celite®, and the filtrate was concentrated. Flash chromatography on silica gel (3% MeOH/CH2Cl2) gave the title compound (1.3 g, 39%): MS (ES) m/e 255 (M+H)+.

Workup

  1. temperatureat reflux overnight
  2. filtrationThe dark mixture was filtered through Celite®
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-084ea8b076b0498e837cf0a5106a25e5
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07741339B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes