3-Bromo-N,N-dimethylaniline → HCID 56924970, compound

HRID 1490497Notes

Reaction equation

HRID 1490497 reaction equation
CN(C)c1cccc(Br)c1>B1Oc2ccccc2O1.CC(C)(O)C(C)(C)O.CCN(CC)CC.Cc1ccccc1.Fc1c(F)c(F)c(B(c2c(F)c(F)c(F)c(F)c2F)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F>CN(C)c1ccc(B2OC(C)(C)C(C)(C)O2)c(Br)c1

Participants

7

Reactant 1

HCID 1401023-Bromo-N,N-dimethylaniline

Product 1

HCID 56924970HCID 56924970, compoundYield 62%

Reagents, catalysts & solvents 5

HCID 6425PinacolReagentHCID 8471TriethylamineReagentHCID 67506CatecholboraneReagentHCID 582056Tris(pentafluorophenyl)boraneCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Prepared from 3-bromo-N,N-dimethylaniline (1i, 40.0 mg, 0.200 mmol, 1.00 equiv) and catBH (36.0 mg, 0.300 mmol, 1.50 equiv) according to GP 1. The title compound was purified by flash column chromatography using cyclohexane/EtOAc/Et3N (30/1/1) as eluent to afford 3i[S4] (40.1 mg, 62%) as a white solid.

Sources & evidence

ORD record
ord-6b8d64e464ac4b9a935d9f94069db1d8
Source dataset
Borylation dataset from Roche

Reaction notes

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