Water → [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonate

HRID 1375178Notes

Reaction equation

HRID 1375178 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[O:15][CH2:14][C@H:13]([CH2:16][OH:17])[O:12][C:8]3=2)[N:3]=1.[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([Br:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19].C(N(CC)CC)C.O>C1(C)C=CC=CC=1.C(O)(C)C.CN(C1C=CC=CN=1)C>[Br:25][C:24]1[CH:26]=[CH:27][C:21]([S:18]([O:17][CH2:16][C@@H:13]2[O:12][C:8]3=[C:9]4[C:4](=[CH:5][CH:6]=[C:7]3[O:15][CH2:14]2)[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]4)(=[O:20])=[O:19])=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 11183845[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]-methanol

Product 1

HCID 20624762[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonateYield 76.9%

Reagents, catalysts & solvents 3

HCID 218852-DimethylaminopyridineCatalystHCID 1140TolueneSolvent2×HCID 3776IsopropanolSolvent

Procedure

A solution of [(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]-methanol (4.0 g, 17.3 mmol), brosyl chloride (4.86 g, 19.0 mmol), dimethylamino pyridine (20 mg, 0.16 mmol) and triethylamine (3.62 mL, 25.8 mmol) in toluene (40 mL) was stirred at 60° C. for 6 h. The reaction mixture was cooled to room temperature then water (20 mL) was added. After 30 min, the two layers were separated. The organic layer was extracted with 8% NaHCO3 (2.0 mL) and H2O (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The solid obtained was dissolved in isopropyl alcohol (50 mL) and toluene (10 mL) at 80° C., cooled to room temperature over 1 h then filtered, washed with (5:1) IPA: toluene (2×5 mL) and dried in a vacuum oven to give 5.99 g (76.9%) of the title compound as an off-white solid.

Workup

  1. customthe two layers were separated
  2. extractionThe organic layer was extracted with 8% NaHCO3 (2.0 mL) and H2O (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe solid obtained
  7. filtrationthen filtered
  8. washwashed with (5:1) IPA
  9. dry with materialtoluene (2×5 mL) and dried in a vacuum oven

Sources & evidence

ORD record
ord-61ba76b4bc0d479ba7f12f94cf184f5a
Source dataset
uspto-grants-2007_01
Patent number
US07166723B2

Reaction notes

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