Sodium hydride → HCID 49857899, compound

HRID 1260518Notes

Reaction equation

HRID 1260518 reaction equation
[C:1]1([CH:7]2[O:12][CH2:11][CH:10]([OH:13])[CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27](Cl)=[N:28][CH:29]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN1C(=O)CCC1>[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]([O:13][CH:10]2[CH2:11][O:12][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:8][CH2:9]2)=[N:28][CH:29]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 743621,3-Dioxan-5-ol, 2-phenyl-HCID 100137175-(Benzyloxy)-2-chloropyridine

Product 1

HCID 49857899HCID 49857899, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2-Phenyl-[1,3]dioxan-5-ol (164 mg. 910 μmol) was dissolved in 5 ml of NMP. Addition of sodium hydride (60% in oil, 72.8 mg, 1.8 mmol) was followed by stirring at RT for 30 min and, after addition of 5-benzyloxy-2-chloropyridine (200 mg, 910 μmol), stirring in a microwave reactor at 200° C. for 1 h. The reaction mixture was concentrated in vacuo, the residue was taken up in ethyl acetate and water, and the organic phase was concentrated. The resulting crude product (386 mg) was directly reacted further.

Workup

  1. stirringstirring in a microwave reactor at 200° C. for 1 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. concentrationwater, and the organic phase was concentrated
  4. customThe resulting crude product (386 mg) was directly reacted further

Sources & evidence

ORD record
ord-e838367944954113ad5c2cdaa24ba304
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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