2,2,2-trifluoro-N-[2-(3-fluorophenyl)ethyl]acetamide → HCID 178431087, compound
Reaction equation
O=C(NCCc1cccc(F)c1)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(c2cc(F)cc(CCNC(=O)C(F)(F)F)c2)OC1(C)C.CC1(C)OB(c2ccc(CCNC(=O)C(F)(F)F)cc2F)OC1(C)CParticipants
7
Reactant 1
Product 2
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 50 °C
Procedure
Following general procedure F using 4e (58.8 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). Stirred in vial at 50 °C for 20 hours. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 12.9:1 meta:para borylation in 98% yield (these numbers include some meta isomer that has also undergone NH borylation). The crude product was purified by silica gel chromatography (15% EtOAc in Petroleum Ether 40‐60 o C) which resulted in the cleavage of the N‐B bond in the NH‐borylation material and gave the title compound (as a 13:1 mixture of meta:para ratio, as determined by 1 H NMR) as a white solid (80 mg, 0.22 mmol, 89%).
Sources & evidence
- ORD record
- ord-061a7ea6016048c1bd19d5920926e678
- Source dataset
- Borylation dataset from Roche
Reaction notes
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