Sodium hydride → HCID 66874736, compound

HRID 249883Notes

Reaction equation

HRID 249883 reaction equation
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1.[CH3:15][O:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[H-].[Na+]>CN1C(=O)CCC1>[CH3:15][O:16][CH:17]1[CH2:22][CH2:21][N:20]([C:2]2[O:3][C:4]3[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=3)[N:6]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 776664-MethoxypiperidineHCID 56924368Methyl 2-chlorobenzo[d]oxazole-4-carboxylate

Product 1

HCID 66874736HCID 66874736, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a solution of methyl 2-chlorobenzoxazole-4-carboxylate (210 mg, 0.99 mmol) in NMP (5 mL) was added 4-methoxypiperidine (230 mg, 1.98 mmol) in NMP (5 mL) at room temperature. NaH was added to the mixture in two portions in 5 min. The mixture was stirred at room temperature for 18 h. The reaction was quenched by adding 10 mL of CH3OH followed by concentration to dryness. The crude material was purified by column chromatography (silica gel, 50% EtOAc in hexane) to afford methyl 2-(4-methoxypiperidin-1-yl)benzoxazole-4-carboxylate (146 mg, 50%) as a yellow solid. MS consistent.

Workup

  1. customThe reaction was quenched
  2. additionby adding 10 mL of CH3OH
  3. concentrationfollowed by concentration to dryness
  4. customThe crude material was purified by column chromatography (silica gel, 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-ffb54e5be2f24c0f8c4d9f858c83b020
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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