4-Methylpyridine-3-Boronic Acid → 3-(2-(2-Fluoroethoxy)-4-nitrophenyl)-4-methylpyridine

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1B(O)O.Br[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[O:21][CH2:22][CH2:23][F:24].CC1C=CN=CC=1C1C=CC=C2C=1C=NN2>>[F:24][CH2:23][CH2:22][O:21][C:13]1[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=1[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

Reactant 3

HCID 27627114-Methylpyridine-3-Boronic Acid

HCID 667156544-(4-methylpyridin-3-yl)-1H-indazole

HCID 867200611-Bromo-2-(2-fluoroethoxy)-4-nitrobenzene

Product 1

HCID 867200623-(2-(2-Fluoroethoxy)-4-nitrophenyl)-4-methylpyridine

Procedure

Intermediate 16C was prepared from Intermediate 1A and Intermediate 16B by the procedure described for the preparation of Intermediate 1C, and was obtained as a beige solid (254 mg, 61% yield). MS (ES): m/z=277.0 [M+H]+.

Sources & evidence

ORD record: ord-ec8d0d63f6a14eca92fc6575b0876260
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916553B2

Reaction notes

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