2-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 58994929, compound

HRID 536939Notes

Reaction equation

HRID 536939 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[C:13](Br)[CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[C:19]1(B2OC(C)(C)C(C)(C)O2)[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=1>CCOC(C)=O.C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([C:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=3)[CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 109326752-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 58994950HCID 58994950, compound

Product 1

HCID 58994929HCID 58994929, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

The title compound was prepared by the Suzuki coupling procedure of Example 16, step (d) using 4-(4-amino-3-bromo-phenyl)-tetrahydro-pyran-4-carboxylic acid methyl ester (as prepared in the Example 16, step (c), 380 mg, 1.21 mmol), and 2-cyclohex-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (277 mg, 1.33 mmol). Silica gel chromatography (0-2% EtOAc/DCM) afforded the title compound (268 mg, 70%) as a white solid. Mass spectrum (ESI, m/z): Calcd. for C19H25NO3, 316.2 (M+H). found 316.2.

Workup

  1. customThe title compound was prepared by the Suzuki coupling procedure of Example 16, step (d)

Sources & evidence

ORD record
ord-08db478173d845d5a55e34e3ae588bb1
Source dataset
uspto-grants-2014_10
Patent number
US08859602B2

Reaction notes

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