5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → 4-(4-Chloro-phenyl)-6-methyl-[2,3';5',3'']terpyridin-6''-ylamine

HRID 1928068Notes

Reaction equation

HRID 1928068 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH:11]=[C:10]([CH3:21])[N:9]=2)[CH:5]=[N:6][CH:7]=1.[NH2:22][C:23]1[CH:28]=[CH:27][C:26](B2OC(C)(C)C(C)(C)O2)=[CH:25][N:24]=1>>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[CH:11]=[C:10]([CH3:21])[N:9]=[C:8]([C:4]3[CH:5]=[N:6][CH:7]=[C:2]([C:26]4[CH:25]=[N:24][C:23]([NH2:22])=[CH:28][CH:27]=4)[CH:3]=3)[CH:13]=2)=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 686930645'-Bromo-4-(4-chloro-phenyl)-6-methyl-[2,3']bipyridinyl

Product 1

HCID 686903324-(4-Chloro-phenyl)-6-methyl-[2,3';5',3'']terpyridin-6''-ylamine

Procedure

The title compound was prepared from 5′-bromo-4-(4-chloro-phenyl)-6-methyl-[2,3′]bipyridinyl (example E.31) (0.600 g, 1.6 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.404 g, 1.8 mmol) according to the general procedure VI. Obtained as a white solid (0.180 g, 29%). MS (ISP) 373.2 [(M+H)+] and 375 [(M+2+H)+];mp 188-192° C.

Sources & evidence

ORD record
ord-70332d0b7a964da293c3fb058d969ff7
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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