Azetidine → 4-(Azetidin-1-yl)benzonitrile

HRID 431

Reaction equation

HRID 431 reaction equation
C1CNC1.N#Cc1ccc(Br)cc1>CC(=O)O.CC(=O)O.CC(C)(C)[O-].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.Cc1ccccc1.[Na+].[Pd]>N#Cc1ccc(N2CCC2)cc1

Participants

7

Reactant 2

HCID 10422AzetidineHCID 12162Benzonitrile, 4-bromo-

Product 1

HCID 700803464-(Azetidin-1-yl)benzonitrileYield 61.99%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 4144353Palladium (II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

4-bromobenzonitrile (1.355 g, 7.44 mmol) and Sodium tert-butoxide (1.073 g, 11.17 mmol) were mixed in toluene (10 mL) and degassed by passing nitrogen for 5 min. Then Azetidine (1 mL, 14.89 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (0.172 g, 0.30 mmol) and Palladium(II) acetate (0.050 g, 0.22 mmol)were added and the mixture was heated in oilbath at 100°C for 15h. The reaction was complete by GCMS. Filtration through celite washing with CH2Cl2 and evaporation gave a crude product (1g). Purification by chromatography on silica (0-50 % EtOAc in heptane) gave the desired product 4-(azetidin-1-yl)benzonitrile (0.730 g, 62.0 %).

Sources & evidence

ORD record
ord-23a7de6b0dd840ca8622691442279b4f
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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