Methylamine → HCID 60199359, compound

HRID 626255Notes

Reaction equation

HRID 626255 reaction equation
[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]([CH2:31][CH3:32])=[C:12]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29]Cl)=[CH:23][CH:22]=3)[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[CH:7][C:5]=2[CH:6]=1.[CH3:33][NH2:34]>CO>[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8](/[C:11](/[CH2:31][CH3:32])=[C:12](\[C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][NH:34][CH3:33])=[CH:23][CH:22]=3)/[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[CH:7][C:5]=2[CH:6]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 123621200HCID 123621200, compound

Product 1

HCID 60199359HCID 60199359, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to the same procedure as example 1, step E described, 2-chloro-5-(1-(4-(2-chloroethoxy)phenyl)-1-(4-methoxyphenyl)but-1-en-2-yl)benzofuran (440 mg, 1.0 eq) was reacted with MeNH2 (30% wt in water, 10 mL) in MeOH (20 mL) under reflux to give the desired (Z)-product (Z and E isomer can be separated via column chromatography). 1H NMR (400 MHz, CDCl3) δ 7.24 (d, J=2.0 Hz, 1H), 7.20 (d, J=8.4 Hz, 1H), 7.15 (d, J=8.8 Hz, 2H), 7.01 (dd, J=8.4 Hz, 2.0 Hz, 1H), 6.88 (d, J=8.8 Hz, 2H), 6.74 (d, J=8.8 Hz, 2H), 6.51 (d, J=8.8 Hz, 2H), 6.45 (s, 1H), 3.92 (t, J=5.2 Hz, 2H), 3.83 (s, 3H), 2.88 (t, J=5.2 Hz, 2H), 2.50 (q, J=7.6 Hz, 2H), 2.45 (s, 3H), 0.92 (t, J=7.6 Hz, 3H); m/z=462[M+1]+.

Workup

  1. temperatureunder reflux
  2. customto give the desired
  3. custom(Z)-product (Z and E isomer can be separated via column chromatography)

Sources & evidence

ORD record
ord-8c5ab069c5c940738dc0c4c6128794ab
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

Loading…