Hydrochloric Acid → HCID 56595571, compound

HRID 2390377Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]#[C:10][C:11]2[CH:16]=[C:15]([S:17]([CH2:20][CH2:21][CH3:22])(=[O:19])=[O:18])[CH:14]=[CH:13][C:12]=2[CH3:23])[CH:3]=1.C[O:25][C:26](=[O:30])[CH:27](Br)[CH3:28].C([O-])([O-])=O.[K+].[K+].[OH-].[Na+].Cl>COCCOC.CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:27]([CH3:28])[C:26]([OH:30])=[O:25])=[C:4]([C:9]#[C:10][C:11]2[CH:16]=[C:15]([S:17]([CH2:20][CH2:21][CH3:22])(=[O:19])=[O:18])[CH:14]=[CH:13][C:12]=2[CH3:23])[CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 4-chloro-2-{[2-methyl-5-(propylsulfonyl)phenyl]ethynyl}phenol (150 mg; 0.43 mmol) and methyl-2-bromopropionate (53 μl; 0.47 mmol) in DME (3 ml) was treated with K2CO3 (89 mg, 69 mmol) and heated at 70° C. for 4.5 hours. The reaction mixture was filtered and the filtrate was concentrated affording a sticky solid, which was dissolved in MeOH (1.5 ml) and treated with a 1 N solution of NaOH in water (129 μl) and the mixture heated for 1 hour at 70° C. A 5 N solution of HCl in water (52 μl) was added and the solvents removed under reduced pressure, to give a residue which was purified by preparative HPLC to give the title compound as a white solid.

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated
customaffording a sticky solid, which
temperaturethe mixture heated for 1 hour at 70° C
customthe solvents removed under reduced pressure
customto give a residue which
customwas purified by preparative HPLC

Sources & evidence

ORD record: ord-3c0644c70ff642729e6d4e9abb6548b3
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273769B2

Reaction notes

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