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1-(Benzyloxy)-4-bromo-2-fluorobenzene → (R)-4-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)propyl)-3-fluoroaniline

HRID 330
Notes
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Reaction equation

HRID 330 reaction equation
C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1>C1COCCO1.CC(=O)O.CC(=O)O.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)C
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 187574911-(Benzyloxy)-4-bromo-2-fluorobenzeneHCID 59302513(R)-2-(tert-butyldimethylsilyloxy)propan-1-amine

Product 1

HCID 58464435(R)-4-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)propyl)-3-fluoroanilineYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagent
HCID 4144353
Palladium (II) acetate
Catalyst
HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

PdOAc2 (0.080 g, 0.36 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.170 g, 0.36 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (1 g, 3.56 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (0.808 g, 4.27 mmol) and cesium carbonate (1.739 g, 5.34 mmol) in anhydrous dioxane (20 mL) at 20°C in a microwave vial. The microwave vial was sealed and the reaction was heated to 120 °C for 10 hours in the microwave reactor and cooled to RT. LCMS indicates mainly starting material **** No further action was taken.

Sources & evidence

ORD record
ord-1df10534bfeb467c9df72e530f4b3ab2
Source dataset
750 AstraZeneca ELN dataset
Original link
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Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes