(Diethylamino)sulfur trifluoride → HCID 68109542, compound

HRID 2179418Notes

Reaction equation

HRID 2179418 reaction equation
CCN(S(F)(F)[F:7])CC.[Cl:10][C:11]1[C:16]2[O:17][C:18]3[CH2:23][CH2:22][N:21]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)[CH:20]([CH2:33]O)[C:19]=3[C:15]=2[CH:14]=[C:13]([S:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)(=[O:37])=[O:36])[CH:12]=1>ClCCl>[Cl:10][C:11]1[C:16]2[O:17][C:18]3[CH2:23][CH2:22][N:21]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)[CH:20]([CH2:33][F:7])[C:19]=3[C:15]=2[CH:14]=[C:13]([S:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)(=[O:37])=[O:36])[CH:12]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 68109544HCID 68109544, compound

Product 1

HCID 68109542HCID 68109542, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DAST (0.4 mL, 3.20 mmol) was slowly added to a stirred solution of the product of step B (180 mg, 0.36 mmol) in anhydrous dichloromethane (12 mL) at 0° C. The resulting solution was allowed to warm to ambient temperature for 3 h then quenched by slow addition of aqueous sodium bicarbonate solution (10 mL). The organic layer was separated and the aqueous solution was further extracted with dichloromethane (2×20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and the filtrate concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 9:1 to 7:3 hexanes/ethyl acetate) to give 6-chloro-1-(fluoromethyl)-2-(4-methoxybenzyl)-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine (90 mg, 51%) as a colorless oil: 1H NMR (CDCl3, 300 MHz) δ 8.14 (d, J=1.2 Hz, 1H), 7.97-7.94 (m, 2H), 7.85 (d, J=1.5 Hz, 1H), 7.61-7.48 (m, 3H), 7.30-7.28 (m, 2H), 6.89-6.86 (m, 2H), 5.76-5.58 (m, 1H), 3.87 (s, 2H), 3.81 (s, 3H), 3.48-3.38 (m, 1H), 3.31-2.89 (m, 5H).

Workup

  1. customthen quenched by slow addition of aqueous sodium bicarbonate solution (10 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous solution was further extracted with dichloromethane (2×20 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was purified by flash column chromatography (SiO2, 9:1 to 7:3 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-9bd1aa40f511456b9cda9de7506bf06b
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

Loading…