Dimethyl Sulfoxide → HCID 57911403, compound

HRID 589005Notes

Reaction equation

HRID 589005 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[C@H:19]1[CH2:29][CH2:28][C@H:27]([OH:30])[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[CH2:20]1.C(N(CC)CC)C>ClCCl>[F:11][C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[CH:19]1[CH2:29][CH2:28][C:27](=[O:30])[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[CH2:20]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 66811576HCID 66811576, compound

Product 1

HCID 57911403HCID 57911403, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
23 °C

Procedure

To a solution of oxalyl chloride (0.91 mL, 11 mmol) in dichloromethane (15 mL) at −65° C. was added DMSO (0.94 mL, 13 mmol), and the mixture was stirred for 30 min. A solution of racemic trans 6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol (prepared according to the procedures described by Leahy, D. K et al Org. Lett. 2012, 14, 4938-4941, 365 mg, 1.33 mmol) in dichloromethane (3 mL) was added drop wise and the resulting solution was stirred at −65° C. for 30 min. Triethylamine (2.55 mL, 18.6 mmol) was added and the reaction mixture was gradually warmed to 23° C. over a period of 4 h, and then partitioned between water and dichloromethane. The organic layer was washed with water (3×), brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with 35% ethyl acetate in petroleum ether to give the title compound as a racemic mixture. MS: m/z=274.2 (M+1).

Workup

  1. stirringthe resulting solution was stirred at −65° C. for 30 min
  2. custompartitioned between water and dichloromethane
  3. washThe organic layer was washed with water (3×), brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with 35% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-709297537034461d959dab909f80813f
Source dataset
uspto-grants-2016_01
Patent number
US09227973B2

Reaction notes

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