2-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 3-Cyclohex-1-enyl-5-nitro-2-(2,2,2-trifluoro-ethoxy)-pyridine

HRID 1253785Notes

Reaction equation

HRID 1253785 reaction equation
Br[C:2]1[C:3]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[C:17]1(B2OC(C)(C)C(C)(C)O2)[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=1>>[C:17]1([C:2]2[C:3]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=1

Participants

3

Reactant 2

HCID 109326752-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 534077653-Bromo-5-nitro-2-(2,2,2-trifluoroethoxy)pyridine

Product 1

HCID 712941573-Cyclohex-1-enyl-5-nitro-2-(2,2,2-trifluoro-ethoxy)-pyridineYield 54.1%

Procedure

This compound was prepared following the same procedure as described for Example 1b using 3-bromo-5-nitro-2-(2,2,2-trifluoro-ethoxy)-pyridine (Example 1a, 1 g, 3.18 mmol) and 2-(1-cyclohexen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAN 141091-37-4, 0.73 g, 3.5 mmol) as starting materials. The title compound (520 mg, 54.0%) was isolated as off white solid; NMR complies.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-5b36144d9fee4af5acfe007d11516ff2
Source dataset
uspto-grants-2013_06
Patent number
US08455501B2

Reaction notes

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