HCID 178471907, compound → HCID 178446973, compound

HRID 2271520Notes

Reaction equation

HRID 2271520 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]=[C:10]([C:16](=[O:21])[CH2:17][CH:18]([CH3:20])[CH3:19])[C:11]([O:13]CC)=O)=[CH:4][CH:3]=1>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]=[CH:9][C:10]([C:16](=[O:21])[CH2:17][CH:18]([CH3:19])[CH3:20])=[C:11]2[OH:13]

Participants

3

Reactant 1

HCID 178471907HCID 178471907, compound

Product 1

HCID 178446973HCID 178446973, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent2×

Procedure

To Dowtherm at 250° C. was added a solution of ethyl 2-[(4-bromophenylamino)methylene]-5-methyl-3-oxohexanoate (700 mg, 6.75 mmol) in Dowtherm (5 mL) portionwise and the reaction mixture was stirred for 1.5 h. The reaction mixture was cooled to room temperature, diluted with hexanes and the resulting precipitate was filtered to afford the desired product (490 mg, 23%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 12.65 (s, 1H), 8.55 (d, J=6.4 Hz, 1H), 8.30 (d, J=2.3 Hz, 1H), 7.88 (dd, J=8.7, 2.3 Hz, 1H), 7.61 (d, J=8.8 Hz, 1H), 2.99 (d, J=6.8 Hz, 2H), 2.21-2.04 (m, 1H), 0.91 (d, J=6.7 Hz, 6H).

Workup

  1. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-84cba42d0c8840ad98466c57e849eece
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

Loading…