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2-Bromo-3-fluoro-6-methylpyridine → 2-(3'-Fluoro-6'-methyl-2,2'-bipyridin-4-yl)isoindoline-1,3-dione

HRID 1522549
Notes
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Reaction equation

HRID 1522549 reaction equation
C([Li])(C)(C)C.Br[C:7]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]([CH3:14])[N:8]=1.Br[C:16]1[CH:21]=[C:20]([N:22]2[C:30](=[O:31])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]2=[O:32])[CH:19]=[CH:18][N:17]=1>O1CCCC1.[Cl-].[Zn+2].[Cl-].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>[F:13][C:12]1[C:7]([C:18]2[CH:19]=[C:20]([N:22]3[C:23](=[O:32])[C:24]4[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:30]3=[O:31])[CH:21]=[CH:16][N:17]=2)=[N:8][C:9]([CH3:14])=[CH:10][CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 248203182-Bromo-3-fluoro-6-methylpyridineHCID 867043642-(2-Bromopyridin-4-yl) isoindoline-1,3-dioneHCID 178418306HCID 178418306, compound

Product 1

HCID 674705142-(3'-Fluoro-6'-methyl-2,2'-bipyridin-4-yl)isoindoline-1,3-dioneYield 44.8%

Reagents, catalysts & solvents 3

HCID 3007855Zincchloride
Catalyst
HCID 178418397HCID 178418397, compoundCatalyst
HCID 8028TetrahydrofuranSolvent3×

Procedure

Tetrahydrofuran (10 mL) was cooled to −78° C. and tert-Butyllithium (4.56 ml, 6.84 mmol) was added, followed by a solution of 2-bromo-3-fluoro-6-methylpyridine (1 g, 5.26 mmol) in tetrahydrofuran (2.5 mL). The reaction mixture was stirred for 30 minutes then zinc(II)chloride (2.58 g, 18.95 mmol) was added and the reaction was warmed to room temperature over 2 hours. A solution of 2-(2-bromopyridin-4-yl) isoindoline-1,3-dione (9) (1.595 g, 5.26 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.608 g, 0.526 mmol) in THF (10 mL) was added and the reaction was stirred at room temperature over night to give a solid which was collected by filtration to give 2-(3′-fluoro-6′-methyl-2,2′-bipyridin-4-yl)isoindoline-1,3-dione as a white solid (786 mg).

Workup

  1. stirringthe reaction was stirred at room temperature over night
  2. customto give a solid which
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-2c81fe2701734e5c9646c0d6bf4fcac9
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09073918B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes