Boron trifluoride etherate → HCID 57814383, compound

HRID 1677662Notes

Reaction equation

HRID 1677662 reaction equation
[BH4-].[Na+].B(F)(F)F.CCOCC.[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2(O)[CH2:25][CH2:24][CH2:23][N:22]3[CH:26]=[N:27][CH:28]=[C:21]23)=[CH:16][CH:15]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:25][CH2:24][CH2:23][N:22]3[CH:26]=[N:27][CH:28]=[C:21]23)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 66933810HCID 66933810, compound

Product 1

HCID 57814383HCID 57814383, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

12.6 mmol of sodium borohydride are suspended in 6 ml of tetrahydrofuran. 19.1 mmol of boron trifluoride ethyl etherate are added dropwise at 0° C. and the reaction mixture is stirred thoroughly for 10 minutes. A suspension of 1.27 mmol of 8-(4-methylsulphanylphenyl) 5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-8-ol in 6 ml of tetrahydrofuran is added and the reaction mixture is stirred at room temperature for 16 hours. The reaction mixture is subsequently poured into saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane (3×). The combined organic phases are dried with sodium sulphate and evaporated. From the residue the title compound is obtained by means of flash chromatography (SiO2 60F) as a white solid. Rf=0.63 (dichloromethane/methanol 9:1); Rt=5.73 (Gradient I).

Workup

  1. additionis added
  2. stirringthe reaction mixture is stirred at room temperature for 16 hours
  3. extractionextracted with dichloromethane (3×)
  4. dry with materialThe combined organic phases are dried with sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-9f097425047041c6a07934cf5f93be83
Source dataset
uspto-grants-2011_08
Patent number
US08008334B2

Reaction notes

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