HCID 178463897, compound → HCID 178463895, compound

HRID 1490821Notes

Reaction equation

HRID 1490821 reaction equation
CCN(CCCc1ccccc1Br)C(=O)C(F)(F)F>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].Cc1ccc(-c2ccc(C)cn2)nc1.[Ir].[Ir]>CCN(CCCc1cc(B2OC(C)(C)C(C)(C)O2)ccc1Br)C(=O)C(F)(F)F.CCN(CCCc1ccc(B2OC(C)(C)C(C)(C)O2)cc1Br)C(=O)C(F)(F)F

Participants

7

Reactant 1

HCID 178463897HCID 178463897, compound

Product 2

HCID 178463894HCID 178463894, compoundYield 28%HCID 178463895HCID 178463895, compoundYield 46%

Reagents, catalysts & solvents 4

HCID 15664HA-44ReagentHCID 2733548Bis(pinacolato)diboraneReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Following general procedure F using N‐(3‐(2‐Bromophenyl)propyl)‐N‐ethyl‐2,2,2‐trifluoroacetamide (169 mg, 0.50 mmol), B2pin2 (190 mg, 0.75 mmol), [Ir(COD)OMe]2 (5.0 mg, 0.0075 mmol) and 5,5’‐ dimethyl‐2,2’‐dipyridyl (2.8 mg, 0.015 mmol) in THF (2.5 mL). The reaction was stirred at 40 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐ dimethoxyethane showed 1:1.4 meta:para borylation in 98% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1‐9:1) to give the title compound as a colourless oil (191 mg, 0.37 mmol, 74%*) as a 1:1.6 meta:para mixture containing 17% B2pin2. *Adjusted yield accounting for B2pin2

Sources & evidence

ORD record
ord-40f10144e8944cd2a0a2cc4587afb33c
Source dataset
Borylation dataset from Roche

Reaction notes

Loading…