Potassium Carbonate → 4-[4-(9-Bromo-2-,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxy]-butyric acid methyl ester

HRID 1069246Notes

Reaction equation

HRID 1069246 reaction equation
[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[C:24]4[C:23]([CH3:25])=[C:22]([CH3:26])[S:21][C:20]=4[C:19]([Br:27])=[C:18]4[C:13]=3[CH:14]=[CH:15][CH:16]=[CH:17]4)[CH:9]=[CH:8][C:7]=2[OH:28])[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34].[H-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1>[CH3:36][O:35][C:33](=[O:34])[CH2:32][CH2:31][CH2:30][O:28][C:7]1[CH:8]=[CH:9][C:10]([C:12]2[C:24]3[C:23]([CH3:25])=[C:22]([CH3:26])[S:21][C:20]=3[C:19]([Br:27])=[C:18]3[C:13]=2[CH:14]=[CH:15][CH:16]=[CH:17]3)=[CH:11][C:6]=1[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 107604Methyl 4-bromobutyrateHCID 184306982-Cyclopentyl-4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenol

Product 1

HCID 701586114-[4-(9-Bromo-2-,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxy]-butyric acid methyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2-cyclopentyl-4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenol (0.30 g, 0.81 mmol), 4-bromobutyric acid, methyl ester (1.5 mL, 13.0 mmol), 60% sodium hydride (0.09 g, 2.3 mmol), potassium carbonate (1.0 g, 7.2 mmol), and anhydrous benzene (2 mL) was heated at 100° for 36 h. Purification by chromatography with hexanes/ethyl acetate gave the title compound as a solid (0.23 g, 52%): NMR (DMSO-d6): δ8.18 (d, J=8 Hz, 1H), 7.62 (ddd, J=2,6,8 Hz, 1H), 7.50-7.41 (m, 2H), 7.16-7.04 (m, 3H), 4.11 (m, 2H), 3.63 (s, 3H), 3.31 (quint, J=8 Hz, 1H), 2.57 (t, J=7 Hz, 2H), 2.42 (s, 3H), 2.07 (quintet, J=7 Hz, 2H), 1.95 (m, 2H), 1.74-1.45 (m containing a singlet at δ1.56, 9H); MS(EI): [M+], 1 bromine isotope pattern, 550/552.

Workup

  1. customPurification by chromatography with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-8b6467a0a5124d17ad09783a9fc6d748
Source dataset
uspto-grants-2001_06
Patent number
US06251936B1

Reaction notes

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