3-Oxetanamine → N-(4-bromo-3-methoxyphenyl)oxetan-3-amine

HRID 632

Reaction equation

HRID 632 reaction equation
COc1cc(I)ccc1Br.NC1COC1>CC(C)(C)[O-].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.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.[Na+].[Pd].[Pd]>COc1cc(NC2COC2)ccc1Br

Participants

7

Reactant 2

HCID 98339233-OxetanamineHCID 121872021-Bromo-4-iodo-2-methoxybenzene

Product 1

HCID 82858132N-(4-bromo-3-methoxyphenyl)oxetan-3-amineYield 35.77%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1-bromo-4-iodo-2-methoxybenzene (0.60 g, 1.92 mmol) dissolved in toluene (15 mL) was treated with oxetan-3-amine (0.140 g, 1.92 mmol), SODIUM TERT-BUTOXIDE (0.221 g, 2.30 mmol), XANTPHOS (0.111 g, 0.19 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.044 g, 0.05 mmol) under nitrogen. The resulting mixture was stirred at 80 °C in a sealed tube for 2 hours. The reaction mixture was diluted with water (10 mL), and extracted with ethyl acetate (3x 20 mL). The organic was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution 0-30% EtOAc in Heptane. Pure fractions were evaporated to dryness to afford N-(4-bromo-3-methoxyphenyl)oxetan-3-amine (0.177 g, 35.8 %) as a beige solid.

Sources & evidence

ORD record
ord-29003fa36fea4ddebef83b29dba29c7c
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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