Water → 5-(6-Fluoro-2,3-dihydro-1H-indol-5-yl)-pent-4-yn-1-ol

HRID 2212549Notes

Reaction equation

HRID 2212549 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:11]#[C:12][CH2:13][CH2:14][CH2:15][OH:16].[BH3-]C#N.[Na+].O.[OH-].[Na+]>CC(O)=O.C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][NH:8]2)=[CH:4][C:3]=1[C:11]#[C:12][CH2:13][CH2:14][CH2:15][OH:16]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 219666015-(6-Fluoro-1H-indol-5-yl)-pent-4-yn-1-ol

Product 1

HCID 219666155-(6-Fluoro-2,3-dihydro-1H-indol-5-yl)-pent-4-yn-1-olYield 73%

Reagents, catalysts & solvents 1

HCID 23437676Trifluoroacetic acid acetateSolvent

Procedure

A solution of 109 mg (0.5 mmol) 5-(6-Fluoro-1H-indol-5-yl)-pent-4-yn-1-ol in 3 ml AcOH/TFA 2:1 was cooled to 0° C., treated with NaCNBH3 and stirred for 1 hour at room temperature. The mixture was poured into icy water, made strongly alkaline by the addition of 2M NaOH, and extracted with EtOAc. Drying of the combined organic layers with MgSO4, evaporation of the solvent, and chromatography on silica gel with CH2Cl2/MeOH 49:1 gave 80 mg (73%) of 5-(6-Fluoro-2,3-dihydro-1H-indol-5-yl)-pent-4-yn-1-ol as a colorless oil, MS: 220 (MH+).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialDrying of the combined organic layers with MgSO4, evaporation of the solvent, and chromatography on silica gel with CH2Cl2/MeOH 49:1

Sources & evidence

ORD record
ord-795f799e963649cbbcc9cad7abd9fe03
Source dataset
uspto-grants-2006_09
Patent number
US07102007B2

Reaction notes

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