(E)-3-(2-Chlorophenyl)acrylaldehyde → HCID 178519054, compound

HRID 1404664Notes

Reaction equation

HRID 1404664 reaction equation
[CH:1](=[C:8]1/[N:9]=[C:10]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])[NH:11][C:12]/1=[O:13])/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1/[CH:29]=[CH:30]/[CH:31]=[O:32]>>[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][CH:30]1[C:31](=[O:32])[O:13][C:12]2[NH:11][C:10]([C:14]3[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=3[F:21])=[N:9][C:8]=2[CH:1]1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6365139(E)-3-(2-Chlorophenyl)acrylaldehydeHCID 136341358(Z)-4-benzylidene-2-(2,5-difluorophenyl)-1H-imidazol-5(4H)-one

Product 1

HCID 178519054HCID 178519054, compoundYield 48%

Procedure

Prepared according to the general procedure using (Z)-4-benzylidene-2-(2,5-difluorophenyl)-1H-imidazol-5(4H)-one and (E)-3-(2-chlorophenyl)acrylaldehyde. The unpurified residue was purified by flash chromatography using 15% EtOAc/hexanes to afford 14 as a white solid (65 mg, 48%). Analytical data for 14: 1H NMR (500 MHz, CDCl3) δ 9.40 (d, J=8.0 Hz, 1H), 7.88 (ddd, J=9.2, 6.1, 3.2 Hz, 1H), 7.39-7.32 (m, 3H), 7.28-7.22 (m, 2H), 7.10-7.03 (m, 2H), 7.01-6.94 (m, 4H), 4.09 (d, J=6.9 Hz, 1H), 3.58 (ddd, J=9.8, 6.8, 4.9 Hz, 1H), 3.31 (dd, J=14.9, 4.9 Hz, 1H), 2.42 (dd, J=14.9, 9.8 Hz, 1H); 13C NMR (CDCl3, 126 MHz) δ 168.6, 159.1 (d, JCF=243.3 Hz), 155.4 (d, JCF=240.2 Hz), 148.9, 140.0, 136.8, 136.5, 134.4, 129.9, 129.3, 129.1, 128.5, 127.9, 127.3, 127.0, 118.3 (dd, JCF=13.0, 9.3 Hz), 117.1 (dd, JCF=25.8, 8.7 Hz), 116.6 (dd, JCF=24.8, 9.5 Hz), 114.5 (dd, JCF=26.8, 3.7 Hz), 110.7 (d, JCF=3.8 Hz), 47.0, 38.6, 32.6; IR (film) cm−1 1772, 1636, 1619, 1598, 1529, 1481, 1463, 1172, 1118, 1079, 875, 813, 766, 741, 697; LRMS (ESI): Mass calcd for [M+H]+ C25H18ClF2N2O2: 451.1. found 451.3; Enantiomeric ratio was measured by chiral phase HPLC (Chiralcel OD-H; 4% IPA/2% MeOH/hexanes 1.0 mL/min, 280 nm), Rt1 (major)=20.7, Rt2 (minor)=23.6 min; er=92:8.

Workup

  1. customPrepared
  2. customThe unpurified residue was purified by flash chromatography

Sources & evidence

ORD record
ord-d2dbcfefcdcc4c4c8810cccfe4f0fdc0
Source dataset
uspto-grants-2014_12
Patent number
US08912341B2

Reaction notes

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