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

HRID 49515Notes

Reaction equation

HRID 49515 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-328b44220787472e859ca24153de000b
Source dataset
uspto-grants-2004_03
Patent number
US06706751B2

Reaction notes

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