2,3-Dimethylthiophene → [2-(4-Bromobenzyl)-4,5-dimethyl-thiophen-3-yl]-(3-cyclopentyl4-hydroxy-phenyl)-methanone

HRID 1841345Notes

Reaction equation

HRID 1841345 reaction equation
[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[S:8][C:9]([CH3:28])=[C:10]([CH3:27])[C:11]=2[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[C:16]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:15]=2)=[O:13])=[CH:4][CH:3]=1.CC1SC=CC=1C>C(Cl)Cl>[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[S:8][C:9]([CH3:28])=[C:10]([CH3:27])[C:11]=2[C:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:15]=2)=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 342952,3-DimethylthiopheneHCID 15895036HCID 15895036, compound

Product 1

HCID 15895037[2-(4-Bromobenzyl)-4,5-dimethyl-thiophen-3-yl]-(3-cyclopentyl4-hydroxy-phenyl)-methanoneYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure in Example 5, step 3 using [2-(4-bromobenzyl)4,5-dimethyl-thiophen-3-yl]-(3-cyclopentyl-4-methoxy-phenyl)-methanone (4.05 g, 8.39 mmol) and 1M boron tribromide/CH2Cl 2(26.0 mL) in CH2Cl2. Purification on Biotage KP-Sil eluting with 15% acetone/hexane gave 2.90 g (74%) of the title compound. (DMSO-d6) δ1.41-1.48 (m, 2 H), 1.59-1.74 (m, 4 H), 1.82 (s, 3 H), 1.89-1.96 (m, 2 H), 2.27 (s, 3 H), 3.20 (quintet, 1 H), 3.84 (s, 2 H), 6.88 (d, 1 H), 7.03 (d, 2 H), 7.39-7.43 (m, 3 H), 7.54 (d, 1 H), 10.47 (s, 1 H).

Workup

  1. customThe title compound was prepared
  2. customPurification on Biotage KP-Sil
  3. washeluting with 15% acetone/hexane

Sources & evidence

ORD record
ord-6255c9a77c774175919b9d2229af688f
Source dataset
uspto-grants-2004_01
Patent number
US06683107B2

Reaction notes

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