1-Phenyl-1-propanone → 4-(1-(6-(3-(Methylamino)propyl)pyridin-3-yl)-2-phenylbut-1-enyl)phenol

HRID 626172Notes

Reaction equation

HRID 626172 reaction equation
C[N:2]([CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=O)[C:20]2[CH:25]=[CH:24][C:23]([O:26]C3CCCCO3)=[CH:22][CH:21]=2)=[CH:15][N:14]=1)[C:3](=O)OC(C)(C)C.[C:34]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=O)[CH2:35][CH3:36]>>[CH3:3][NH:2][CH2:10][CH2:11][CH2:12][C:13]1[N:14]=[CH:15][C:16]([C:19]([C:20]2[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=2)=[C:34]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:35][CH3:36])=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 71481-Phenyl-1-propanoneHCID 121266711tert-butyl methyl(3-(5-(4-(tetrahydro-2H-pyran-2-yloxy)benzoyl)pyridin-2-yl)propyl)carbamate

Product 1

HCID 781355594-(1-(6-(3-(Methylamino)propyl)pyridin-3-yl)-2-phenylbut-1-enyl)phenolYield 20%

Procedure

Following general procedure of McMurry reaction as described in example 1, step B, tert-butyl methyl(3-(5-(4-(tetrahydro-2H-pyran-2-yloxy)benzoyl)pyridin-2-yl)propyl)carbamate (100 mg, 0.22 mmol) was reacted with propiophenone (88 mg, 0.66 mmol) to give 16 mg desired product (20% yield, Z/E=1/1). m/z=373[M+1]+.

Workup

  1. customgeneral procedure of McMurry reaction

Sources & evidence

ORD record
ord-6cec653e6ed14eafa32ca0fc4d7b4b05
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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