HCID 178523282, compound → HCID 178431052, compound
Reaction equation
O=C(NCCCc1ccccc1C(F)(F)F)C(F)(F)F>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CCCC[N+](CCCC)(CCCC)CCCC.C[OH2+].C[OH2+].Cc1ccc(-c2ccc(CS(=O)(=O)[O-])cn2)nc1.[Ir].[Ir]>CC1(C)OB(c2ccc(C(F)(F)F)c(CCCNC(=O)C(F)(F)F)c2)OC1(C)C.CC1(C)OB(c2ccc(CCCNC(=O)C(F)(F)F)c(C(F)(F)F)c2)OC1(C)CParticipants
7
Reactant 1
Product 2
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 50 °C
Procedure
Following general procedure F using 2,2,2‐trifluoro‐N‐(3‐(2‐(trifluoromethyl)phenyl)propyl)acetamide (74.8 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and 1A (3.8 mg, 0.0075 mmol) in THF (1.25 mL). The reaction was stirred at 50 °C for 20 hours before cooling and the solventsremoved. Analysis of crude 1 H NMR using internalstandard 1,2‐dimethoxyethane showed 19.5:1 meta:para borylation in 97% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1) to give the title compound (as a 19:1 mixture of meta:para ratio, as determined by 1 H NMR) as a white solid (103.5 mg, 0.24 mmol, 97%).
Sources & evidence
- ORD record
- ord-dec2e741f7424e7abbb9a7e0981c2d90
- Source dataset
- Borylation dataset from Roche
Reaction notes
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