2-Chloro-5-cyanophenylboronic acid → 4-Chloro-3-[5-[(2-cyclohexylethylamino)methyl]pyridin-2-yl]benzonitrile

HRID 561354Notes

Reaction equation

HRID 561354 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][C:20]=1B(O)O>>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][C:20]=1[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH:9][CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 27632792-Chloro-5-cyanophenylboronic acidHCID 59544849(6-Bromopyridin-3-ylmethyl)-(2-cyclohexylethyl)amine

Product 1

HCID 595448504-Chloro-3-[5-[(2-cyclohexylethylamino)methyl]pyridin-2-yl]benzonitrile

Procedure

Using the procedure outlined in Preparation 13, (6-bromopyridin-3-ylmethyl)-(2-cyclohexylethyl)amine and 2-chloro-5-cyanophenyl boronic acid were converted to the title compound: RT=2.79 min; m/z (ES+)=354.1 [M+H]+.

Sources & evidence

ORD record
ord-e2a931c6ce8d45aab77ff6e34eebed71
Source dataset
uspto-grants-2011_11
Patent number
US08063247B2

Reaction notes

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