Triphenylphosphine → 6-Methoxy-2-(4-Methoxyphenyl)-3-(4-[1-Ethylpiperidin-3-oxy]benzoyl)benzo[b]thiophene

HRID 1107577Notes

Reaction equation

HRID 1107577 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11](=[O:19])[C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)=[C:9]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[S:8][C:7]=2[CH:28]=1.[CH2:29]([N:31]1[CH2:36][CH2:35][CH2:34][CH:33](O)[CH2:32]1)[CH3:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOC(/N=N/C(OCC)=O)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11](=[O:19])[C:12]3[CH:13]=[CH:14][C:15]([O:18][CH:33]4[CH2:34][CH2:35][CH2:36][N:31]([CH2:29][CH3:30])[CH2:32]4)=[CH:16][CH:17]=3)=[C:9]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[S:8][C:7]=2[CH:28]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 1145241-Ethyl-3-piperidinolHCID 98651972-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiophene

Product 1

HCID 98922456-Methoxy-2-(4-Methoxyphenyl)-3-(4-[1-Ethylpiperidin-3-oxy]benzoyl)benzo[b]thiopheneYield 17%

Reagents, catalysts & solvents 1

HCID 5462977Diethyl azodicarboxylateCatalyst

Procedure

6-Methoxy-2-(4-methoxyphenyl)-3-(4-hydroxybenzoyl)benzo[b]thiophene (1.17 g, 3.00 mmol), 1-ethyl-3-hydroxypiperidine (775 mg, 6.00 mmol), triphenylphosphine (1.57 g, 6.00 mmol), and DEAD (6.0 nmol) were converted to product by the procedure of Example 11 to give 256 mg of the title compound. Yield: 17%. MS(FD) 501(M+). EA calculated for C30H31NO4S: C, 71.83; H, 6.23; N, 2.79. Found: C, 72.10; H, 6.47; N, 3.07.

Sources & evidence

ORD record
ord-b007b875686a4a678cc4fddce14e92cc
Source dataset
uspto-grants-2000_05
Patent number
US06060488

Reaction notes

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