Sodium borohydride → {2-[3-(2-Fluoro-pyridin-3-ylmethyl)-benzo[b]thiophen-2-yl]-ethyl}-dimethyl-amine

HRID 746631Notes

Reaction equation

HRID 746631 reaction equation
[BH4-].[Na+].[CH3:3][N:4]([CH3:25])[CH2:5][CH2:6][C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[C:8]=1[CH:16]([C:18]1[C:19]([F:24])=[N:20][CH:21]=[CH:22][CH:23]=1)O>C(O)(C(F)(F)F)=O>[F:24][C:19]1[C:18]([CH2:16][C:8]2[C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[S:11][C:7]=2[CH2:6][CH2:5][N:4]([CH3:3])[CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58591576[2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-(2-fluoro-pyridin-3-yl)-methanol

Product 1

HCID 58591584{2-[3-(2-Fluoro-pyridin-3-ylmethyl)-benzo[b]thiophen-2-yl]-ethyl}-dimethyl-amineYield 28.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

A suspension of NaBH4 (0.11 g, 2.9 mmol) in 7 mL TFA was stirred at room temperature for 15 minutes. A solution of [2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-(2-fluoro-pyridin-3-yl)-methanol (0.12 g, 0.36 mmol) in 6 mL TFA was added slowly. The mixture was stirred at room temperature for 48 h. The solvent was evaporated and water and ammonium hydroxide were added at 0° C. until pH=9. The solution was extracted with EtOAc (3×) and washed with water/ammonium hydroxide (30/1 v/v). The combined organic layers were concentrated and 0.12 g of crude material was obtained. Purification by Mass triggered HPLC afforded 32 mg of {2-[3-(2-fluoro-pyridin-3-ylmethyl)-benzo[b]thiophen-2-yl]-ethyl}-dimethyl-amine (Compound 24-2) (MH+=315.0, tR=4.50, Method 2).

Workup

  1. stirringThe mixture was stirred at room temperature for 48 h
  2. customThe solvent was evaporated
  3. additionwater and ammonium hydroxide were added at 0° C. until pH=9
  4. extractionThe solution was extracted with EtOAc (3×)
  5. washwashed with water/ammonium hydroxide (30/1 v/v)
  6. concentrationThe combined organic layers were concentrated
  7. custom0.12 g of crude material was obtained
  8. customPurification by Mass

Sources & evidence

ORD record
ord-66ad853668fe4fdf98cf0d89b603c424
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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