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N-Boc-4-chloro-3-fluoroaniline → HCID 130053535, compound

HRID 1491240
Notes
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Reaction equation

HRID 1491240 reaction equation
CC(C)(C)OC(=O)Nc1ccc(Cl)c(F)c1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CC1(C)OBOC1(C)C.COC(C)(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>CC(C)(C)OC(=O)Nc1cc(F)c(Cl)cc1B1OC(C)(C)C(C)(C)O1.CC(C)(C)OC(=O)Nc1ccc(Cl)c(F)c1B1OC(C)(C)C(C)(C)O1
ParticipantsConditionsSources & evidenceReaction notes

Participants

8

Reactant 1

HCID 59652188N-Boc-4-chloro-3-fluoroaniline

Product 2

HCID 124221708Carbamic acid, N-[4-chloro-3-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-, 1,1-dimethylethyl esterYield 16%HCID 130053535HCID 130053535, compoundYield 52%

Reagents, catalysts & solvents 5

HCID 2733548Bis(pinacolato)diboraneReagentHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
50 °C

Sources & evidence

ORD record
ord-d704933bec314454a9f0b189aec17ed1
Source dataset
Borylation dataset from Roche
DOI
10.1021/ja303443m

Reaction notes

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On this pageParticipantsConditionsSources & evidenceReaction notes