Benzaldehyde → HCID 22965709, compound

HRID 568175Notes

Reaction equation

HRID 568175 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([C:6]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:7]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[NH:8]2)=[CH:4][CH:3]=1.[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:25]1([CH2:24][NH:1][C:2]2[N:10]=[C:9]3[C:5]([C:6]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)=[C:7]([C:11]4[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=4)[NH:8]3)=[CH:4][CH:3]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 9926492HCID 9926492, compound

Product 1

HCID 22965709HCID 22965709, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

6-Amino-3-(4-pyridyl)-2-(4-fluorophenyl)-7-aza-indole (17) (100 mg, 0.329 mmol), benzaldehyde (100 ml, 0.987 mmol), and 1,2-dichloroethane (20 mL) were allowed to stir for 15 min followed by the addition of sodium triacetoxyborohydride (139 mg, 0.658 mmol) as a solid. After 16 h at 23° C., the reaction was partitioned between ethyl acetate (200 mL) and satd bicarbonate (80 mL). The organic layer was washed with brine (80 mL), and dried (Na2SO4). After concentration in vacuo, a portion of the residue was purified by preparative chromatography to afford 6-(phenylmethylamino)-3-(4-pyridyl)-2-(4-fluoro phenyl)-7-aza-indole (144):Mass Spectrum (CI) 395 (MH+).

Workup

  1. waitAfter 16 h at 23° C.
  2. customthe reaction was partitioned between ethyl acetate (200 mL) and satd bicarbonate (80 mL)
  3. washThe organic layer was washed with brine (80 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationAfter concentration in vacuo
  6. customa portion of the residue was purified by preparative chromatography

Sources & evidence

ORD record
ord-95ce951f665f4dbbb936f5604389d327
Source dataset
uspto-grants-2001_01
Patent number
US06180643B2

Reaction notes

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