6-Fluoropyridine-2-carboxaldehyde → (E)-2-Cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)-3-(6-fluoropyridin-2-yl)acrylamide

HRID 2406584Notes

Reaction equation

HRID 2406584 reaction equation
Br[C:2]1[N:7]=[C:6](/[CH:8]=[C:9](\[C:31]#[N:32])/[C:10]([NH:12][CH:13]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[CH:19][CH:18]=2)[CH2:14][CH2:15][CH3:16])=[O:11])[CH:5]=[CH:4][CH:3]=1.[F:33]C1N=C(C=O)C=CC=1>>[C:31](/[C:9](=[CH:8]\[C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([F:33])[N:7]=1)/[C:10]([NH:12][CH:13]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[CH:19][CH:18]=1)[CH2:14][CH2:15][CH3:16])=[O:11])#[N:32]

Participants

3

Reactant 2

HCID 106067416-Fluoropyridine-2-carboxaldehydeHCID 56947930(E)-3-(6-Bromopyridin-2-yl)-2-cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)acrylamide

Product 1

HCID 56947932(E)-2-Cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)-3-(6-fluoropyridin-2-yl)acrylamideYield 61%

Procedure

The title compound was prepared by using a similar procedure as described for the preparation of 33 except that 6-fluoropicolinaldehyde was used instead of 6-bromopicolinaldehyde. This produced crude product which was purified by flash silica gel column chromatography, eluting with 4:96 methanol/dichloromethane, to give 34 (105 mg, 61%) as a yellow oil: MS (ES+) m/z 439.2 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. customThis produced crude product which
  3. customwas purified by flash silica gel column chromatography
  4. washeluting with 4:96 methanol/dichloromethane

Sources & evidence

ORD record
ord-905c394118eb433aa9a1e27b6edae30d
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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