HCID 87773155, compound → HCID 178486936, compound

HRID 1490806Notes

Reaction equation

HRID 1490806 reaction equation
COc1ccccc1CCCNC(=O)C(F)(F)F>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>COc1cc(B2OC(C)(C)C(C)(C)O2)ccc1CCCNC(=O)C(F)(F)F.COc1ccc(B2OC(C)(C)C(C)(C)O2)cc1CCCNC(=O)C(F)(F)F

Participants

7

Reactant 1

HCID 87773155HCID 87773155, compound

Product 2

HCID 178486936HCID 178486936, compoundYield 61%HCID 178488279HCID 178488279, compoundYield 30%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Following general procedure F using 2,2,2‐trifluoro‐N‐(3‐(2‐methoxyphenyl)propyl)acetamide (65.3 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and dtbpy (2.0 mg, 0.0075 mmol) in THF (1.25 mL). The reaction was stirred at 70 °C for 20 hours before cooling and the solventsremoved. Analysis of crude 1 H NMR using internalstandard 1,2‐dimethoxyethane showed 1:2.0 meta:para borylation in 91% yield.

Sources & evidence

ORD record
ord-f34ac206ce6a45c19bab8d12076928a6
Source dataset
Borylation dataset from Roche

Reaction notes

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