2-Furanacrolein → HCID 178519057, compound

HRID 1404666Notes

Reaction equation

HRID 1404666 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.[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1/[CH:27]=[CH:28]/[CH:29]=[O:30]>>[F:21][C:15]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[C:10]1[NH:11][C:12]2[O:13][C:29](=[O:30])[CH:28]([CH2:27][C:23]3[O:22][CH:26]=[CH:25][CH:24]=3)[CH:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:8]=2[N:9]=1

Participants

3

Reactant 2

HCID 15495212-FuranacroleinHCID 136341358(Z)-4-benzylidene-2-(2,5-difluorophenyl)-1H-imidazol-5(4H)-one

Product 1

HCID 178519057HCID 178519057, compoundYield 66%

Procedure

Prepared according to the general procedure using (Z)-4-benzylidene-2-(2,5-difluorophenyl)-1H-imidazol-5(4H)-one and (E)-3-(furan-2-yl)acrylaldehyde. The unpurified residue was purified by flash chromatography using 15% EtOAc/hexanes to afford 16 as an off-white solid (80 mg, 66%). Analytical data for 16: 1H NMR (500 MHz, CDCl3) δ 9.45 (d, J=8.1 Hz, 1H), 7.90 (ddd, J=9.2, 6.1, 3.2 Hz, 1H), 7.37 (ap d, J=1.2 Hz, 1H), 7.37-7.27 (m, 3H), 7.11-7.01 (m, 3H), 7.01-6.94 (m, 1H), 6.34 (dd, J=3.2, 1.9 Hz, 1H), 6.02 (d, J=2.9 Hz, 1H), 4.20 (d, J=6.9 Hz, 1H), 3.70 (ddd, J=10.3, 6.8, 4.1 Hz, 1H), 3.30 (ddd, J=15.9, 4.2, 1.2 Hz, 1H), 2.48 (dd, J=15.8, 10.4 Hz, 1H); 13C NMR (CDCl3, 126 MHz) δ 168.4, 159.1 (d, JCF=243.8 Hz), 155.4 (dd, JCF=241.2, 2.2 Hz), 151.8, 149.1, 141.6, 136.7, 136.5, 129.2, 128.3, 128.0, 118.4 (dd, JCF=12.8, 9.2 Hz), 117.1 (dd, JCF=25.6, 8.8 Hz), 116.6 (dd, JCF=24.9, 9.6 Hz), 114.5 (dd, JCF=26.9, 3.7 Hz), 110.7 (d, JCF=3.9 Hz), 110.4, 107.6, 44.9, 38.5, 25.6; IR (film) cm−1 1770, 1636, 1620, 1529, 1482, 1464, 1452, 1173, 1117, 1008, 919, 902, 885, 875, 814, 766, 736, 700; LRMS (ESI): Mass calcd for [M+H]+ C23H17F2N2O3: 407.1. found 407.3; Enantiomeric ratio was measured by chiral phase HPLC (Chiralcel OD-H; 5% IPA/3% MeOH/hexanes 0.5 mL/min, 280 nm), Rt1 (major)=32.4, Rt2 (minor)=36.4 min; er=98:2.

Workup

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

Sources & evidence

ORD record
ord-f4ffe45cedd74c699c9f79799bbbdbdf
Source dataset
uspto-grants-2014_12
Patent number
US08912341B2

Reaction notes

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