Triethylamine → 6-(2,3-Difluorophenyl)-5-fluoro-9-((triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine

HRID 589006Notes

Reaction equation

HRID 589006 reaction equation
COCCN(S(F)(F)[F:11])CCOC.[F:14][C:15]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=1[CH:22]1[CH2:32][CH2:31][CH:30]([O:33][Si:34]([CH:41]([CH3:43])[CH3:42])([CH:38]([CH3:40])[CH3:39])[CH:35]([CH3:37])[CH3:36])[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:24]2[CH:23]1O.C(N(CC)CC)C>ClCCCl>[F:14][C:15]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=1[CH:22]1[CH2:32][CH2:31][CH:30]([O:33][Si:34]([CH:41]([CH3:43])[CH3:42])([CH:38]([CH3:40])[CH3:39])[CH:35]([CH3:37])[CH3:36])[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:24]2[CH:23]1[F:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 671170715H-Cyclohepta[b]pyridin-5-ol, 6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-9-[[tris(1-methylethyl)silyl]oxy]-, (5R,6S,9R)-

Product 1

HCID 1317344546-(2,3-Difluorophenyl)-5-fluoro-9-((triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
23 °C

Procedure

Deoxo-Fluor® (0.148 g, 0.670 mmol) was added dropwise to a solution of (5S,6S,9R and 5R,6R,9S)-6-(2,3-difluorophenyl)-9-((triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ol (prepared according to the procedures described by Leahy, D. K et al Org. Lett. 2012, 14, 4938-4941, 0.30 g, 0.67 mmol) and triethylamine (0.093 mL, 0.67 mmol) in 1,2-dichloroethane (2 mL) at 0° C. The resulting mixture was gradually warmed to 23° C. and stirred for 2 h, then partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane (3×). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel, eluting with 35% dichloromethane in petroleum ether to give the title compound as a racemic mixture. MS: m/z=450.2 (M+1).

Workup

  1. customprepared
  2. customat 0° C
  3. custompartitioned between saturated aqueous sodium bicarbonate solution and dichloromethane (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel
  8. washeluting with 35% dichloromethane in petroleum ether

Sources & evidence

ORD record
ord-28f4eb007dce412bbaecd0fc61cc7621
Source dataset
uspto-grants-2016_01
Patent number
US09227973B2

Reaction notes

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