Benzaldehyde → benzyl-{2-[3-(2-methoxy-ethoxy)-phenyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-amine

HRID 502799Notes

Reaction equation

HRID 502799 reaction equation
[BH4-].[CH3:2][O:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([C:13]2[NH:22][C:16]3=[N:17][CH:18]=[C:19]([NH2:21])[CH:20]=[C:15]3[CH:14]=2)[CH:10]=[CH:11][CH:12]=1.[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CO>[CH2:23]([NH:21][C:19]1[CH:20]=[C:15]2[CH:14]=[C:13]([C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([O:6][CH2:5][CH2:4][O:3][CH3:2])[CH:8]=3)[NH:22][C:16]2=[N:17][CH:18]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 28123BorohydrideHCID 684656192-[3-(2-methoxy-ethoxy)-phenyl]-1H-pyrrolo[2,3-b]pyridin-5-ylamine

Product 1

HCID 16061683benzyl-{2-[3-(2-methoxy-ethoxy)-phenyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-amineYield 7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Polymer supported borohydride (706 mg, 1.8 mmol) was added to a mixture of 2-[3-(2-methoxy-ethoxy)-phenyl]-1H-pyrrolo[2,3-b]pyridin-5-ylamine (50 mg, 0.18 mmol) and benzaldehyde (18mg, 0.18 mmol) in methanol (3 mL). The mixture was stirred for 16 hours, filtered, concentrated in vacuo and purified by preparative HPLC to afford benzyl-{2-[3-(2-methoxy-ethoxy)-phenyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-amine (4.4 mg, 7%)

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-eb5e2057c06b42b5a2f9ef0350934c31
Source dataset
uspto-grants-2010_08
Patent number
US07776878B2

Reaction notes

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