4-Toluenesulfonyl chloride → HCID 90409573, compound

HRID 594037Notes

Reaction equation

HRID 594037 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][OH:15])[CH2:9]2)[CH:3]=1.[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl.O>[CH3:23][C:22]1[CH:24]=[CH:25][C:19]([S:16]([O:15][CH2:14][C@H:10]2[O:11][CH2:12][CH2:13][N:8]([C:4]3[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][N:5]=3)[CH2:9]2)(=[O:18])=[O:17])=[CH:20][CH:21]=1

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 90409286HCID 90409286, compound

Product 1

HCID 90409573HCID 90409573, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-(4-(4-bromopyridin-2-yl)morpholin-2-yl)methanol (1.0 equiv.), tosyl chloride (1.0 equiv.), triethylamine (1.40 equiv.) and N,N-dimethylpyridin-4-amine (0.1 equiv.) in dichloromethane (0.1 M) at RT. The resulting mixture was stirred at RT for 18 hours. The reaction mixture was then diluted with water and the aqeuous layer was separated and washed sequentially with NaOH (1 M), water, brine dried over sodium sulfate then concentrated in vacuo to yield (S)-(4-(4-bromopyridin-2-yl)morpholin-2-yl)methyl 4-methylbenzenesulfonate in 56% yield. LCMS (m/z) (M+H)=427.1/429.0, Rt=0.77 min.

Workup

  1. customat RT
  2. customthe aqeuous layer was separated
  3. washwashed sequentially with NaOH (1 M), water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-175d701e76fd4fb8a951172a89b2ba44
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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