4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde → HCID 178420311, compound

HRID 1969524Notes

Reaction equation

HRID 1969524 reaction equation
Cl[C:2]1[C:7]([CH:8]=O)=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12.Cl.[CH2:14]([N:21]1[CH2:26][CH2:25][CH2:24][CH:23]([NH:27][NH2:28])[CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CCCCO>[CH2:14]([N:21]1[CH2:26][CH2:25][CH2:24][CH:23]([N:27]2[C:2]3=[C:3]4[CH:12]=[CH:11][NH:10][C:4]4=[N:5][CH:6]=[C:7]3[CH:8]=[N:28]2)[CH2:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 242292744-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehydeHCID 67216964HCID 67216964, compound

Product 1

HCID 178420311HCID 178420311, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (0.40 g, 2.21 mmol, Adesis) and 1-benzyl-3-hydrazinylpiperidine hydrochloride (1.39 g, 4.43 mmol) were suspended in n-BuOH (11.1 mL). The mixture was heated at about 90° C. for about 3 h and then heated at about 120° C. for about 5 h. The reaction mixture was cooled to ambient temperature and the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography eluting with a gradient of 0-5% MeOH in DCM to yield 1-(1-benzylpiperidin-3-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.105 g, 14%) as a brown oil: LC/MS (Table 1, Method b) Rt=1.53 min; MS m/z: 332 (M+H)+.

Workup

  1. temperatureheated at about 120° C. for about 5 h
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with a gradient of 0-5% MeOH in DCM

Sources & evidence

ORD record
ord-9a63a009d0c24e579d23bdd007125eb1
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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