Pyridine → HCID 86757351, compound

HRID 1595116Notes

Reaction equation

HRID 1595116 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[C:13][CH2:14][S:15][CH2:16][C:17]#[C:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[OH:29].N1C=CC=CC=1.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C(Cl)Cl>[CH3:36][S:37]([O:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]#[C:17][CH2:16][S:15][CH2:14][C:13]#[C:12][CH2:11][CH2:10][CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][S:37]([CH3:36])(=[O:39])=[O:38])(=[O:39])=[O:38]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 53911460HCID 53911460, compound

Product 1

HCID 86757351HCID 86757351, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 82 (0.2 g, 0.9 mmol) in 2 mL of anhydrous CH2Cl2 at 0° C. was added anhydrous pyridine (71 mg, 0.9 mmol) and methylsulfonyl chloride (0.1 g, 0.9 mmol) under argon (FIG. 2N). The solution was stirred at room temperature for 6 h. The reaction was carefully quenched with water and extracted with CH2Cl2 (3×10 mL). The combined organic extracts were washed with water, dried (MgSO4), and concentrated in vacuo. Chromatography on silica gel (EtOAc:hexanes, 5:95) gave the desired methylsulfonyloxy derivative 124 as a colorless oil (0.22 g, 84%). 1H NMR (CDCl3) δ7.51-7.53 (dd, 1 H, J=7.6 Hz and 2.6 Hz, ArH), 7.40-7.42 (dd, 1 H, J=7.9 Hz and 2.8 Hz, ArH), 7.26-7.30 (m, 2 H, ArH), 3.66 (t, 2 H, J=1.3 Hz CH2), 3.24 (s, 3 H, CH3), 2.11-2.13 (m, 2 H, CH2), 1.26-1.41 (m, 4 H, CH2), 0.84-0.87 (t, 3 H, J=7.1 Hz, CH3); 13C NMR (CDCl3) δ147.63, 130.77, 129.18, 127.82, 127.59, 123.20, 84.74, 74.54, 38.50, 30.52, 21.97, 21.77, 18.37, 13.53.

Workup

  1. customThe reaction was carefully quenched with water
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d466ab67d02a4185bd625de4d8a0275e
Source dataset
uspto-grants-2001_09
Patent number
US06284918B1

Reaction notes

Loading…