Sodium Hydroxide → HCID 59864771, compound

Participants

Reaction Conditions

Reaction Steps

2-(4-(4-Amino-2-propyl-1H-indol-5-yloxy)-3-chlorophenyl)acetic acid, 2-(4-(4-amino-3-ethyl-2-methyl-1H-indol-5-yloxy)-3-chlorophenyl)acetic acid and 2-(4-(6-amino-3-ethyl-2-methyl-1H-indol-5-yloxy)-3-chlorophenyl)acetic acid (7.3). A solution of the mixture of regioisomers 7.2 (1.30 g, 3.34 mmol) and tin chloride dihydrate 3.02 g, 13.4 mmol) dissolved in ethyl acetate (10 mL) was heated to 90° C. (external temperature, oil bath) in a capped vial overnight. The reaction solution was poured into aqueous 1N sodium hydroxide solution and the resulting bi-phase passed through a pad of Celite, rinsing with water and ethyl acetate. The filtrate was acidified to pH<4 with 1N hydrochloric acid solution and the organic layer separated and washed with water and brine then stirred over magnesium sulfate, filtered and the filtrate concentrated in vacuo on a rotary evaporator. The regioisomers were isolated by semi-preparative reversed phase HPLC to afford regioisomer A as a brown solid and regioisomer B as a brown solid and regioisomer C as a brown solid. LC-MS ESI (pos.) m/z: 359.0 (M+H).

Provenance & Evidence