2-(Cyclopropylmethoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 86670729, compound

HRID 878102Notes

Reaction equation

HRID 878102 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]([CH3:25])[C:9](=[O:24])[C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1.[CH:26]1([CH2:29][O:30][C:31]2[C:36](B3OC(C)(C)C(C)(C)O3)=[CH:35][CH:34]=[CH:33][N:32]=2)[CH2:28][CH2:27]1>CCCCCCC.CCOC(C)=O>[CH:26]1([CH2:29][O:30][C:31]2[C:36]([C:2]3[CH:7]=[CH:6][N:5]=[CH:4][C:3]=3[N:8]([CH3:25])[C:9](=[O:24])[C:10]3[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=3)=[CH:35][CH:34]=[CH:33][N:32]=2)[CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 177501932-(Cyclopropylmethoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 86670697N-(4-iodopyridin-3-yl)-N-methyl-3,5-bis(trifluoromethyl)benzamide

Product 1

HCID 86670729HCID 86670729, compound

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 72, from N-(4-iodo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide (example 98, intermediate a) and 2-(cyclopropylmethoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (CAS RN 848243-26-5) and using a gradient of n-heptane:EtOAc (100:0 to 30:70) for the chromatographic purification. Light yellow oil (63%). MS (ESI): m/z=498.146 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-1fd836ec06724742b52d6ddaecec4208
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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