Sodium methylsulfide → HCID 67973766, compound

HRID 1184701Notes

Reaction equation

HRID 1184701 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([C:22]4[C:23]([CH3:29])=[N:24][C:25](Cl)=[CH:26][CH:27]=4)[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[CH3:30][S:31]C.[Na]>C(OCC)(=O)C>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([C:22]4[C:23]([CH3:29])=[N:24][C:25]([S:31][CH3:30])=[CH:26][CH:27]=4)[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 86593196Sodium methylsulfide2×HCID 86674890HCID 86674890, compound

Product 1

HCID 67973766HCID 67973766, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-[5-(6-chloro-2-methyl-pyridin-3-yl)-2,3-dihydro-benzofuran-2-yl]-piperidine-1-carboxylic acid isopropyl ester (160 mg) and sodium methyl sulfide (84 mg) in N,N-dimtehylformamide (1.6 mL) is stirred for 4 h at 80° C. Three more portions of sodium methyl sulfide (28 mg each) are added over the course of two days while stirring the reaction mixture at 80° C. until completion of the reaction. The reaction mixture is diluted with ethyl acetate, washed with water and brine, and concentrated in vacuo. The crude product is used without further purification for the next reaction step. LC (method 6): tR=1.31 min; Mass spectrum (ESI+): m/z=427 [M+H]+.

Workup

  1. stirringwhile stirring the reaction mixture at 80° C.
  2. customuntil completion of the reaction
  3. washwashed with water and brine
  4. concentrationconcentrated in vacuo
  5. customThe crude product is used without further purification for the next reaction step

Sources & evidence

ORD record
ord-658ca1faff9041d29d73a943db07bd97
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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