2-Bromobenzaldehyde → 4-(2-Bromophenyl)-2,6-dimethyl-5-(4-methyl-1,3-thiazol-2-yl)-1,4-dihydropyridine-3-carbonitrile

HRID 1951549Notes

Reaction equation

HRID 1951549 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][C:11]1[N:12]=[C:13]([CH2:16][C:17]([CH3:19])=O)[S:14][CH:15]=1.[NH2:20]/[C:21](/[CH3:25])=[CH:22]\[C:23]#[N:24]>C(O)(C)C>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:16]([C:13]2[S:14][CH:15]=[C:11]([CH3:10])[N:12]=2)=[C:17]([CH3:19])[NH:20][C:21]([CH3:25])=[C:22]1[C:23]#[N:24]

Participants

5

Reactant 3

HCID 811292-BromobenzaldehydeHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 179309881-(4-Methyl-1,3-thiazol-2-yl)propan-2-one

Product 1

HCID 1358449664-(2-Bromophenyl)-2,6-dimethyl-5-(4-methyl-1,3-thiazol-2-yl)-1,4-dihydropyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

150 mg (0.811 mmol) of 2-bromobenzaldehyde, 126 mg (0.811 mmol) of the compound from example 4A and 67 mg (0.811 mmol) of 3-aminocrotononitrile are dissolved in 4 ml of isopropanol and stirred at the reflux temperature overnight. After cooling to room temperature, the volatile components are removed in a rotary evaporator, the crude material is taken up in 5 ml of ethyl acetate, and the precipitated product is then filtered off 190 mg (61% of theory) of the title compound are obtained.

Workup

  1. customthe volatile components are removed in a rotary evaporator
  2. filtrationthe precipitated product is then filtered off 190 mg (61% of theory) of the title compound
  3. customare obtained

Sources & evidence

ORD record
ord-eb8fc712dd8c4c87bd1be10ce6e2a2c3
Source dataset
uspto-grants-2013_03
Patent number
US08404723B2

Reaction notes

Loading…