Hydrochloric Acid → HCID 86698705, compound

HRID 338364Notes

Reaction equation

HRID 338364 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]([F:26])[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]([F:26])[CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86698704HCID 86698704, compound

Product 1

HCID 86698705HCID 86698705, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of methyl 6-chloro-5-[3-fluoro-4-(3-hydroxypropoxy)phenyl]-1H-indole-3-carboxylate (85 mg, 0.23 mmol) in methanol (5 mL) and water (2 mL) was added sodium hydroxide (90 mg, 2.3 mmol). The reaction mixture was heated at 70° C. and stirred for 24 hours. 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 (31 mg, 52% yield) as a white solid. MS (AP−) 386.1 (M+Na)−. 1H NMR (400 MHz, DMSO-d6) δ 12.14 (s, 1H), 11.98 (s, 1H), 8.08 (s, 1H), 7.925 (s, 1H), 7.62 (s, 1H), 7.25-7.15 (m, 3H), 4.59 (t, 1H), 4.16 (t, 2H), 3.58 (q, 2H), 1.90 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-d1cdb8d33ada44dbba4645ef7901860d
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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