4,5,6,7-Tetrahydro-2-methylthiazolo[5,4-c]pyridine → Potassium (2-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-5-yl)methyltrifluoroborate

HRID 1422616Notes

Reaction equation

HRID 1422616 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH2:5][NH:6][CH2:7][CH2:8][C:9]=2[N:10]=1.Br[CH2:12][B-:13]([F:16])([F:15])[F:14].[K+:17]>O1CCCC1>[CH3:1][C:2]1[S:3][C:4]2[CH2:5][N:6]([CH2:12][B-:13]([F:16])([F:15])[F:14])[CH2:7][CH2:8][C:9]=2[N:10]=1.[K+:17]

Participants

4

Reactant 2

HCID 150176454,5,6,7-Tetrahydro-2-methylthiazolo[5,4-c]pyridineHCID 23690312Potassium (bromomethyl)trifluoroborate

Product 1

HCID 131732225Potassium (2-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-5-yl)methyltrifluoroborate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine (3.00 g), potassium bromomethyltrifluoroborate (3.91 g), KHCO3 (1.95 g), KI (0.32 g), and tetrahydrofuran (25 mL) is stirred at reflux temperature for 4 h. After cooling to room temperature, the solvent is evaporated and the residue is suspended in acetone. The insoluble salts are separated by filtration and the filtrate is treated with diethyl ether. The precipitate is separated by filtration and dried to give the title compound (alternatively, the crude product is purified by chromatography on silica gel using dichloromethane and methanol as eluent). Mass spectrum (ESI−): m/z=235 [M]−.

Workup

  1. temperatureat reflux temperature for 4 h
  2. customthe solvent is evaporated
  3. customThe insoluble salts are separated by filtration
  4. additionthe filtrate is treated with diethyl ether
  5. customThe precipitate is separated by filtration
  6. customdried

Sources & evidence

ORD record
ord-d6a96364eff5492a90bbc36ab79dee6c
Source dataset
uspto-grants-2015_01
Patent number
US08927531B2

Reaction notes

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