6-Bromopyridine-2-carbaldehyde → 6-(4-(Trifluoromethyl)phenyl)picolinaldehyde

HRID 1472881Notes

Reaction equation

HRID 1472881 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1N=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:15]1[N:20]=[C:19]([CH:21]=[O:22])[CH:18]=[CH:17][CH:16]=1.Br[C:24]1N=C(C=O)C(F)=CC=1>CO>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:24]=[CH:7][C:6]([C:15]2[N:20]=[C:19]([CH:21]=[O:22])[CH:18]=[CH:17][CH:16]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 27570096-Bromopyridine-2-carbaldehydeHCID 164142386-Bromo-3-fluoropyridine-2-carbaldehydeHCID 251342782-(Trifluoromethyl)pyridine-5-boronic Acid

Product 1

HCID 247300896-(4-(Trifluoromethyl)phenyl)picolinaldehyde

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared using procedure similar to that described for Example 28A, substituting 4-(trifluoromethyl)phenylboronic acid for 6-(trifluoromethyl)pyridin-3-ylboronic acid and 6-bromopicolinaldehyde for 6-bromo-3-fluoropicolinaldehyde. MS (ESI+) m/z 283.9 (M+H+MeOH); 1H NMR (300 MHz, DMSO-d6) δ 10.09 (s, 1H), 8.46-8.38 (m, 3H), 8.21 (t, J=7.7, 1H), 8.00-7.89 (m, 3H).

Sources & evidence

ORD record
ord-2d7acec76413473aa5cd9235be820b5c
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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