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Sodium Carbonate → 6-((S)-2-Amino-3-phenylpropylamino)-3-(3-methylphenyl)-2-(4-pyridyl)pyridine

HRID 566711
Notes
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Reaction equation

HRID 566711 reaction equation
[NH2:1][C@@H:2]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:3][NH:4][C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[C:8](Br)=[CH:7][CH:6]=1.[CH3:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[NH2:1][C@@H:2]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:3][NH:4][C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[C:8]([C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([CH3:25])[CH:31]=2)=[CH:7][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339503-Tolylboronic acidHCID 158963226-((S)-2-Amino-3-phenylpropylamino)-3-bromo-2-(4-pyridyl)pyridine

Product 1

HCID 158963236-((S)-2-Amino-3-phenylpropylamino)-3-(3-methylphenyl)-2-(4-pyridyl)pyridine

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 1140TolueneSolvent

Procedure

To a stirred, degassed mixture of 6-((S)-2-Amino-3-phenylpropylamino)-3-bromo-2-(4-pyridyl)pyridine (4.2 gm, 10.9 mmole), 3-methylbenzene boronic acid (1.8 gm, 13 mmole), in aqueous 2 M Na2CO3 (50 mL) and toluene (50 mL) at rt was added Pd(PPh3)4(400 mg, 0.35 mmole). The mixture was heated to reflux for 12 hrs, cooled to rt, and extracted with toluene. The combined organic layers were washed with brine, concentrated and purified (SiO2, CH2Cl2/MeOH/NH4OH: 100/11/8) to give the title compound. MS (m/z): Calcd. C26H26N4 (M+): 394, found (M+H)+: 395.1.

Workup

  1. customTo a stirred, degassed
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 12 hrs
  4. extractionextracted with toluene
  5. washThe combined organic layers were washed with brine
  6. concentrationconcentrated
  7. custompurified (SiO2, CH2Cl2/MeOH/NH4OH: 100/11/8)

Sources & evidence

ORD record
ord-2ab876132206401c9c935b1b945de397
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06174901B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes