Hydrochloric Acid → HCID 86698708, compound

HRID 338366Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13]C)=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][OH:25])=[C:17]([O:26][CH3:27])[CH:16]=1.[OH-].[Na+].Cl>CO.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][OH:25])=[C:17]([O:26][CH3:27])[CH:16]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of methyl 6-chloro-5-[4-(3-hydroxypropoxy)-3-methoxyphenyl]-1H-indole-3-carboxylate (92 mg, 0.24 mmol) in MeOH (5 mL) and water (2 mL) was added NaOH (94 mg, 2.4 mmol). The reaction mixture was heated at 70° C. and stirred for 24 hours. TLC (petroleum ether/ethyl acetate=1:1) showed the reaction was complete. The mixture was acidified by 1N HCl to pH 4 and extracted with ethyl acetate (10 mL×3). The combined organic layers was dried over sodium sulfate, filtered, and concentrated in vacuo to give a brown residue. It was purified by preparative HPLC to give the title compound (35 mg, 35% yield) as a white solid. MS (AP−) 398.1 (M+Na)−. 1H NMR (400 MHz, DMSO-d6) δ 11.93 (s, 1H), 8.07 (s, 1H), 7.93 (s, 1H), 7.60 (s, 1H), 7.02 (d, 1H), 6.97 (s, 1H) 6.89 (dd, 1H), 4.04 (t, 2H), 3.77 (s, 3H), 3.51 (t, 2H), 1.88 (m, 2H).

Workup

extractionextracted with ethyl acetate (10 mL×3)
dry with materialThe combined organic layers was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customto give a brown residue
customIt was purified by preparative HPLC

Sources & evidence

ORD record: ord-7dcb804343994e80bc407d51f22ee5ad
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889730B2

Reaction notes

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