Sodium Hydroxide → (6-bromo-pyridin-3-ylmethyl)-[5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-amine

HRID 509969Notes

Reaction equation

HRID 509969 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Cl:19])[CH:18]=[C:13]3[C:12]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([NH2:27])=[N:25][CH:26]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[Br:28][C:29]1[N:34]=[CH:33][C:32]([CH:35]=O)=[CH:31][CH:30]=1.C([BH3-])#N.[OH-].[Na+].[Cl-].[NH4+]>C(O)C.C(O)(=O)C>[Br:28][C:29]1[N:34]=[CH:33][C:32]([CH2:35][NH:27][C:24]2[CH:23]=[CH:22][C:21]([CH2:20][C:12]3[C:13]4[C:14](=[N:15][CH:16]=[C:17]([Cl:19])[CH:18]=4)[NH:10][CH:11]=3)=[CH:26][N:25]=2)=[CH:31][CH:30]=1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 498716Cyano-borohydrideHCID 117692346-Bromo-3-pyridinecarboxaldehydeHCID 576192232-Pyridinamine, 5-[[5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]methyl]-

Product 1

HCID 86653328(6-bromo-pyridin-3-ylmethyl)-[5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-amineYield 31%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

To 5-(1-benzenesulfonyl-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamine (120, 80.0 mg, 0.200 mmol) in 2.00 mL of ethanol and 0.10 mL of acetic acid, 6-bromo-pyridine-3-carbaldehyde (121, 100.0 mg, 0.538 mmol) and silica supported cyanoborohydride (0.50 g, 1.21 mmol/g) were added. The reaction was heated at 110° C. for 25 minutes in microwave. Sodium hydroxide (2.0 mL, 6.0 M aqueous) was added and the reaction heated at 100° C. for 10 minutes in microwave, then poured into aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was separated, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane. Appropriate fractions were combined and the solvent removed under vacuum to provide the desired compound (P-2002, 26.6 mg). MS (ESI) [M+H+]+=427.7, 429.7.

Workup

  1. additionwere added
  2. temperaturethe reaction heated at 100° C. for 10 minutes in microwave
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe resulting material was purified by silica gel column chromatography
  9. washeluting with 20% ethyl acetate in hexane
  10. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-a7c0f1cb83b540849955abb66db96789
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

Loading…