Sodium Sulfite → 5-[4-(azetidin-3-yl)phenyl]-6-chloro-1H-indole-3-carboxylic acid

HRID 338443Notes

Reaction equation

HRID 338443 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[CH:10]=[CH:9][C:8]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][C:19]=3[Cl:20])[NH:16][CH:15]=[C:14]4[CH:21]=[O:22])=[CH:7][CH:6]=2)[CH2:2]1.P([O-])(O)(O)=[O:24].[Na+].Cl([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>CC(=CC)C.CC(O)(C)C.O>[NH:1]1[CH2:4][CH:3]([C:5]2[CH:10]=[CH:9][C:8]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][C:19]=3[Cl:20])[NH:16][CH:15]=[C:14]4[C:21]([OH:24])=[O:22])=[CH:7][CH:6]=2)[CH2:2]1

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 866987735-[4-(azetidin-3-yl)phenyl]-6-chloro-1H-indole-3-carbaldehyde

Product 1

HCID 866987745-[4-(azetidin-3-yl)phenyl]-6-chloro-1H-indole-3-carboxylic acidYield 10.2%

Reagents, catalysts & solvents 1

HCID 230840282-Methyl-2-butene t-butanol waterSolvent

Procedure

To 5-[4-(azetidin-3-yl)phenyl]-6-chloro-1H-indole-3-carbaldehyde (94 mg, 0.30 mmol) in 2-methyl-2-butene/t-BuOH/H2O (v/v/v=1/1/1, 4 mL) was added sodium dihydrogen phosphate (364 mg, 3.04 mmol) and sodium chlorite (274 mg, 3.04 mmol) at room temperature. The resulting mixture was stirred at room temperature for 24 hours. To the reaction mixture was added sodium sulfite (383 mg, 3.04 mmol), then concentrated in vacuo and purified via reverse phase HPLC to give the title compound (10 mg, 10% yield). 1H NMR (400 MHz, CD3OD) δ 8.03-80.4 (d, 2H), 7.62 (s, 1H), 7.48-7.52 (m, 4H), 4.44-4.48 (m, 2H), 4.32-4.34 (m, 3H).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-f9d2e966535044ffb724f3d65b9250c3
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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