Water → HCID 78135729, compound

HRID 626117Notes

Reaction equation

HRID 626117 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:13]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][CH3:16])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10]NC.[C:30]([Cu])#[N:31].O.[CH3:34][N:35](C=O)C>>[OH:29][C:26]1[CH:27]=[CH:28][C:23]([C:13]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][NH:31][CH3:30])=[C:2]([CH:3]=2)[C:34]#[N:35])=[C:14]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:15][CH3:16])=[CH:24][CH:25]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 78135728HCID 78135728, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 78135729HCID 78135729, compoundYield 6%

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 4-(1-(3-bromo-4-(2-(methylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol (150 mg, 1.0 eq) in 5 mL DMF was added CuCN (36 mg, 1.2 eq) at rt. The mixture was then heated at 120° C. overnight, poured into water, and the resulting mixture was extracted with EtOAc. The extract was washed with water and brine, dried, concentrated, and purified by column chromatography with CH2Cl2:MeOH(NH3)=1:1 to give the desired product (10 mg, 6% yield, Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.36 (s, 1H), 6.99-7.21 (m, 7H), 6.90 (d, J=8.8 Hz, 1H), 6.81 (d, J=8.8 Hz, 1H), 6.68 (d, J=8.8 Hz, 1H), 6.49 (d, J=8.8 Hz, 1H), 4.32 (t, J=5.6 Hz, 1H), 4.20 (t, J=5.2 Hz, 1H), 3.46 (t, J=5.6 Hz, 1H), 3.30 (t, J=5.2 Hz, 1H), 3.29 (s, 3H), 2.40-2.50 (m, 2H), 0.90 (t, J=5.6 Hz, 3H); m/z=399 [M+1]+.

Workup

  1. extractionthe resulting mixture was extracted with EtOAc
  2. washThe extract was washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. custompurified by column chromatography with CH2Cl2

Sources & evidence

ORD record
ord-1c256fa1a5cc485bba6f0b4d0d222680
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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