Sodium cyanoborohydride → 9-{[3-(5-fluoro-1H-indol-3-yl)propyl]amino}-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]isoquinolin-1(8H)-one

HRID 1727393Notes

Reaction equation

HRID 1727393 reaction equation
[NH2:1][CH:2]1[CH2:16][O:15][C:5]2=[CH:6][CH:7]=[C:8]3[C:13]([C:12](=[O:14])[NH:11][CH2:10][CH2:9]3)=[C:4]2[CH2:3]1.[F:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[C:21]2[CH2:27][CH2:28][CH:29]=O.[BH3-]C#N.[Na+]>C(O)(=O)C.CO>[F:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[C:21]2[CH2:27][CH2:28][CH2:29][NH:1][CH:2]1[CH2:16][O:15][C:5]2=[CH:6][CH:7]=[C:8]3[C:13]([C:12](=[O:14])[NH:11][CH2:10][CH2:9]3)=[C:4]2[CH2:3]1

Participants

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 118461793-(5-fluoro-1H-indol-3-yl)propanalHCID 575676709-amino-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]isoquinolin-1(8H)-one

Product 1

HCID 462277549-{[3-(5-fluoro-1H-indol-3-yl)propyl]amino}-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]isoquinolin-1(8H)-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a mixture of 9-amino-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]isoquinolin-1(8H)-one (46) (130 mg, 0.596 mmol), 3-(5-fluoro-1H-indol-3-yl)propanal ((2), 113 mg, 0.596 mmol) in acetic acid (70 μl) and methanol (20 ml) was added NaBH3CN (75 mg, 1.19 mmol) in portions. The resulting mixture was stirred for 2 hr. The solvent was removed in vacuo and the residue was dissolved in methylene chloride. The organic solution was washed with 1N NaOH and saturated NaCl before being dried over with Na2SO4. Concentration of organic solution gave the crude compound, which was purified on silica gel (100% EtOAc) to give the desired compound, which was treated with 1 equivalent of etherate HCL to form HCl salt for title compound. MS (APPI) m/z 394.4.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washThe organic solution was washed with 1N NaOH and saturated NaCl
  4. dry with materialbefore being dried over with Na2SO4
  5. customConcentration of organic solution gave the crude compound, which
  6. customwas purified on silica gel (100% EtOAc)

Sources & evidence

ORD record
ord-6739cf9661714229a53e30ab143d85b7
Source dataset
uspto-grants-2009_02
Patent number
US07495111B2

Reaction notes

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