Tetrahydrofuran → HCID 84076342, compound

HRID 475119Notes

Reaction equation

HRID 475119 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:11]([NH2:13])=O.C1COCC1>>[F:1][C:2]1[C:3]([CH2:11][NH2:13])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 86694700HCID 86694700, compound

Product 1

HCID 84076342HCID 84076342, compoundYield 86.4%

Procedure

A mixture of 5-fluoro-1H-indole-4-carboxamide (240 mg, 1.35 mmol) and a solution of BH3 in THF (1.0 M, 16 mL, 16 mmol) was stirred at RT for 18 hours. The reaction was quenched with a solution of HCl (1.0 M, 20 mL) followed by stirring at RT for 1.5 h. The pH of the reaction mixture was adjusted to about ca. 10 by adding a satd. aq. Na2CO3. The mixture was extracted with EtOAc (50 mL×3). The combined organic layers were washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with DCM/MeOH/TEA (10:1:0.1) to afford (5-fluoro-1H-indol-4-yl)methanamine (107) as a yellow solid (190 mg, 86.4%). MS (ESI): m/z=148.1 [M−16]+.

Workup

  1. customThe reaction was quenched with a solution of HCl (1.0 M, 20 mL)
  2. additionby adding a satd
  3. extractionThe mixture was extracted with EtOAc (50 mL×3)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by SiO2 chromatography
  9. washeluting with DCM/MeOH/TEA (10:1:0.1)

Sources & evidence

ORD record
ord-425ebdb2800d436eb73966c2322adcee
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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