Sodium Hydroxide → HCID 57950259, compound

HRID 1020660Notes

Reaction equation

HRID 1020660 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=O.[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([CH2:17][CH2:18][NH2:19])=[CH:13][NH:14]2)=[CH:10][CH:9]=1.BrC1C=CC=C2C=1C(CCN)=CN2.[OH-].[Na+]>Cl>[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]3[CH2:17][CH2:18][NH:19][CH:3]([C:2]([OH:6])=[O:5])[C:13]=3[NH:14]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 180714Ethanamine, 2-(6-bromo-1H-indol-3-yl)-HCID 10944501HCID 10944501, compoundHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 57950259HCID 57950259, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
25 °C

Procedure

Glyoxylic acid monohydrate (3.69 g, 40.1 mmol) was added to a solution of a 2:1 mixture of 2-(6-bromo-1H-indol-3-yl)ethanamine and 2-(4-bromo-1H-indol-3-yl)ethanamine (7.38 g, 30.9 mmol) in 0.4 N HCl (50 mL), and the resulting solution was stirred at 25° C. for 30 min. The solution was adjusted to pH 3.5 with 6 N NaOH solution, and the resulting tan suspension was stirred at 25° C. for 22 h. The suspension was adjusted to pH 5 with 6 N NaOH solution, and the resulting suspension was filtered. The filtered solid was dried under reduced pressure to afford 3.85 g (42%) of a 2:1 mixture of the title compound and an undesired regioisomer as a tan solid: 1H NMR (300 MHz, DMSO-d6) δ 10.90 (s, 1H), 9.00 (br s, 1H), 7.63 (s, 1H), 7.33 (d, J=8.4 Hz, 1H), 7.12-7.04 (m, 1H), 4.66 (s, 1H), 3.50-2.70 (m, 4H).

Workup

  1. stirringthe resulting tan suspension was stirred at 25° C. for 22 h
  2. filtrationthe resulting suspension was filtered
  3. customThe filtered solid was dried under reduced pressure
  4. customto afford

Sources & evidence

ORD record
ord-172451d01f904065933737f59cf403b2
Source dataset
uspto-grants-2014_05
Patent number
US08716308B2

Reaction notes

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