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

HRID 1107579Notes

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.[N:29]1([C@@H:34]2[CH2:39][CH2:38][CH2:37][CH2:36][C@H:35]2O)[CH2:33][CH2:32][CH2:31][CH2:30]1.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:35]4[CH2:36][CH2:37][CH2:38][CH2:39][CH:34]4[N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]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

Reactant 4

HCID 11776Triphenylphosphine

HCID 5462977Diethyl azodicarboxylate

HCID 98651972-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiophene

HCID 10103566rel-(1R,2R)-2-(1-Pyrrolidinyl)cyclohexanol

Product 1

HCID 99589906-Methoxy-2-(4-Methoxyphenyl)-3-(4-[2-Pyrrolidin-1-ylcyclohexoxy]benzoyl)benzo[b]thiopheneYield 35%

Procedure

6-Methoxy-2-(4-methoxyphenyl)-3-(4-hydroxybenzoyl)benzo[b]thiophene (1.27 g, 3.25 mmol), trans-2-pyrrolidinylcyclohexanol (1.10 g, 6.50 mmol), triphenylphosphine (1.70 g, 6.50 mmol), and DEAD (6.50 mmol) were converted to product by the procedure of Example 11 to give 615 mg of the title compound. Yield: 35%. MS(FD) 541(M+). IR (CHCl3) ν max 3009, 2940, 1645, 1597, 1476, 1254, 1166.

Sources & evidence

ORD record: ord-f804d86175fc43019aafcc809870b97c
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06060488

Reaction notes

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