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(3S)-(-)-3-(Dimethylamino)pyrrolidine → 4-chloro-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]benzonitrile

HRID 81
Notes
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Reaction equation

HRID 81 reaction equation
CN(C)[C@H]1CCNC1.N#Cc1ccc(Cl)cc1Br>Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>CN(C)[C@H]1CCN(c2cc(Cl)ccc2C#N)C1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 234985242-Bromo-4-chlorobenzonitrile

Product 1

HCID 1784182124-chloro-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]benzonitrileYield 69.34%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 634876Binap, (A+-)-
Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromo-4-chlorobenzonitrile (500 mg, 2.31 mmol), (S)-N,N-dimethylpyrrolidin-3-amine (317 mg, 2.77 mmol), cesium carbonate (1505 mg, 4.62 mmol), tris(dibenzylideneacetone)dipalladium(0) (212 mg, 0.23 mmol) and BINAP (288 mg, 0.46 mmol) in toluene (15 mL) was stirred at 100 °C for overnight. Conc. in vacuo, the residue was purified with ISCO (100% ethyl acetate to 30% methanol in ethyl acetate) to yield a light yellow solid as (S)-4-chloro-2-(3-(dimethylamino)pyrrolidin-1-yl)benzonitrile (400 mg, 69.3 %).

Sources & evidence

ORD record
ord-58bee23c6bfd4e46abec561eea6c720a
Source dataset
750 AstraZeneca ELN dataset
Original link
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Reaction notes

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