Sodium Bicarbonate → 1189746-38-0

HRID 2079754Notes

Reaction equation

HRID 2079754 reaction equation
COCCN(S(F)(F)[F:11])CCOC.[Br:14][C:15]1[N:20]=[C:19]([C:21](O)([CH3:23])[CH3:22])[CH:18]=[CH:17][CH:16]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:17][CH2:18][CH2:19][CH:21]([CH3:23])[CH3:22].[Br:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([C:21]([F:11])([CH3:23])[CH3:22])[N:20]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 227143012-(6-Bromopyridin-2-yl)propan-2-ol

Product 2

HCID 78922-MethylpentaneHCID 838550801189746-38-0Yield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add (bis(2-methoxyethyl)amino)sulfur trifluoride (2.05; mL, 11.11; mmol) dropwise to a cooled solution of 2-(6-bromo-pyridin-2-yl)-propan-2-ol (2; g, 9.26 mmol) in dichloromethane (46.3; mL) at −78° C. Upon addition, warm to room temperature and stir overnight. Add a saturated aqueous solution of sodium bicarbonate and stir until gas evolution stops. Filter through a 50; mL hydrophobic IST Phase Separator Frit®, concentrate and purify by silica gel chromatography, gradient eluting from 3:97; to 5:95; and then to 10:90; using dichloromethane:iso-hexane to give the title compound as a colorless liquid (5.13; g, 71%). 1H NMR (CDCl3) δ 1.66; (s, 3H), 1.73; (s, 3H), 7.37; (dd, 2H), 7.53; (m, 2H). 19F NMR (CDCl3) δ-143.37; (s, 1F).

Workup

  1. additionUpon addition
  2. stirringstir until gas evolution
  3. filtrationFilter through a 50
  4. concentrationmL hydrophobic IST Phase Separator Frit®, concentrate
  5. custompurify by silica gel chromatography
  6. washgradient eluting from 3:97

Sources & evidence

ORD record
ord-375ea295dd644829a26dfe526a94904a
Source dataset
uspto-grants-2011_04
Patent number
US07932274B2

Reaction notes

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