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Acetic Acid → 6-fluoro-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 1727394
Notes
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Reaction equation

HRID 1727394 reaction equation
[NH2:1][CH:2]1[CH2:17][O:16][C:5]2=[C:6]([F:15])[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:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2[CH2:28][CH2:29][CH:30]=O.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[F:15][C:6]1[CH:7]=[C:8]2[C:13](=[C:4]3[CH2:3][CH:2]([NH:1][CH2:30][CH2:29][CH2:28][C:22]4[C:21]5[C:25](=[CH:26][CH:27]=[C:19]([F:18])[CH:20]=5)[NH:24][CH:23]=4)[CH2:17][O:16][C:5]=13)[C:12](=[O:14])[NH:11][CH2:10][CH2:9]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 118461793-(5-fluoro-1H-indol-3-yl)propanalHCID 690647709-amino-6-fluoro-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]isoquinolin-1(8H)-one

Product 1

HCID 159808536-fluoro-9-{[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

1
HCID 887MethanolSolvent

Procedure

To a solution of 9-amino-6-fluoro-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]isoquinolin-1(8H)-one (49) (110 mg, 0.47 mmol) in anhydrous methanol (7 ml) was added 3-(5-fluoro-1H-indol-3-yl) propanal (2) (89 mg, 0.47 mmol), acetic acid (0.060 ml), and NaBH3CN (59 mg, 0.930 mmol). Resulting reaction mixture was stirred at room temperature for 3 hr. The solvent was removed in vacuo and the residue was re-dissolved in CH2Cl2 (120 ml). The solution was washed with 1 N NaOH and H2O, saturated. NaCl. The organic solution was separated, dried over Na2SO4, then concentrated in vacuo. The crude compound was purified on silica gel eluting with 80% EtOAc/Hexane to yield the title compound. MS (ES) m/z 410.2.

Workup

  1. customResulting
  2. customreaction mixture
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was re-dissolved in CH2Cl2 (120 ml)
  5. washThe solution was washed with 1 N NaOH and H2O
  6. customThe organic solution was separated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe crude compound was purified on silica gel eluting with 80% EtOAc/Hexane

Sources & evidence

ORD record
ord-c447ee97622749b5ae73495508baaa73
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07495111B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes