3-Bromo-9-(phenylsulfonyl)-9H-pyrrolo[2,3-b:5,4-c′]dipyridin-5-ol → HCID 58364979, compound

HRID 60334Notes

Reaction equation

HRID 60334 reaction equation
C1(S([N:10]2[C:14]3[CH:15]=[N:16][CH:17]=[C:18]([OH:19])[C:13]=3[C:12]3[CH:20]=[C:21]([Br:24])[CH:22]=[N:23][C:11]2=3)(=O)=O)C=CC=CC=1>Cl>[Br:24][C:21]1[CH:22]=[N:23][C:11]2[NH:10][C:14]3[CH:15]=[N:16][CH:17]=[C:18]([OH:19])[C:13]=3[C:12]=2[CH:20]=1

Participants

3

Reactant 1

HCID 672494313-Bromo-9-(phenylsulfonyl)-9H-pyrrolo[2,3-b:5,4-c′]dipyridin-5-ol

Product 1

HCID 58364979HCID 58364979, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
125 °C

Procedure

9-Benzenesulfonyl-3-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-5-ol (4.0 g, 9.32 mmol) was dissolved in concentrated hydrochloric acid (100 mL) and heated in an autoclave at 125° C. for 40 hours. The mixture was allowed to cool to ambient temperature then evaporated in-vacuo. The resultant residue was loaded onto a 50 g SCX-2 cartridge which was washed with methanol, then 2N ammonia in methanol. Appropriate fractions were combined and concentrated in-vacuo to afford the title compound as a light brown solid (2.44 g, 99%). LCMS (Method B): RT=2.70 min, M+H+=264/266. 1H NMR (400 MHz, DMSO-d6): 12.25 (s, 1H), 8.61 (d, J=2.4 Hz, 1H), 8.58 (d, J=2.4 Hz, 1H), 8.42 (s, 1H), 8.04 (s, 1H).

Workup

  1. temperatureto cool to ambient temperature
  2. customthen evaporated in-vacuo
  3. washwas washed with methanol
  4. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-df4a235912d34b3c87c81dc6d94c6522
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

Loading…