HCID 57928435, compound → 1H-Pyrrolo[2,3-b]pyridine-5-carboxamide

HRID 1360203Notes

Reaction equation

HRID 1360203 reaction equation
OC12CC3CC(CC(C3N[C:13]3[C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=[C:15]4[NH:22][CH:23]=[CH:24][C:14]=34)C1)C2>Br>[NH:22]1[C:15]2=[N:16][CH:17]=[C:18]([C:19]([NH2:21])=[O:20])[CH:13]=[C:14]2[CH:24]=[CH:23]1

Participants

3

Reactant 1

HCID 57928435HCID 57928435, compound

Product 1

HCID 457903211H-Pyrrolo[2,3-b]pyridine-5-carboxamideYield 172.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

4-[(5-Hydroxyadamantan-2-yl)amino]-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (100 mg) was dissolved in 45% aqueous HBr (0.5 ml), and the mixture was refluxed for 1.5 hours. The reaction solution was cooled, and the obtained solid was collected by filtration and washed with water. The obtained solid was dissolved in dichloromethane and methanol, and purified by silica gel column chromatography (chloroform:methanol) to obtain 4-[5-bromoadamantan-2-yl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (85 mg).

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. temperatureThe reaction solution was cooled
  3. filtrationthe obtained solid was collected by filtration
  4. washwashed with water
  5. dissolutionThe obtained solid was dissolved in dichloromethane
  6. custommethanol, and purified by silica gel column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-c45b1d2df6334fbf97d0ac34b3004348
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

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