Sodium Sulfate → 1-(4-Fluoro-1H-indol-2-yl)methanamine

HRID 1051349Notes

Reaction equation

HRID 1051349 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([NH2:13])=O)[NH:6]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH2:11][NH2:13])[NH:6]2

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 86711990HCID 86711990, compound

Product 1

HCID 573556491-(4-Fluoro-1H-indol-2-yl)methanamineYield 33.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 36 (130 mg, 0.730 mmol) in anhydrous THF (5.0 mL) was added LiAlH4 (138 mg, 3.65 mmol) at 0-5° C. The reaction mixture was heated at 80° C. overnight. After cooling to RT, the mixture was treated with aq. Na2SO4. The resulting mixture was extracted with EtOAc (3×10 mL). The combined organic layers were dried and concentrated. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc/TEA (10:10:0.5) to afford 40 mg (33%) of (4-fluoro-1H-indol-2-yl)methanamine (38) as a pale yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 11.22 (s, 1H), 7.14 (d, J=8.0 Hz, 1H), 6.97 (m, 1H), 6.70 (m, 1H), 6.28 (s, 1H), 3.82 (s, 2H). LCMS (ESI) m/z: 148.1 [M+H−17]+.

Workup

  1. temperatureAfter cooling to RT
  2. extractionThe resulting mixture was extracted with EtOAc (3×10 mL)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customThe residue was purified by SiO2 chromatography
  6. washeluting with petroleum ether/EtOAc/TEA (10:10:0.5)

Sources & evidence

ORD record
ord-72092b6009694c72b53994a60c1f5376
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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