4-(Bromoacetyl)pyridine hydrobromide → 4-(4-Pyridin-4-yl-thiazol-2-ylmethoxy)piperidine-1-carboxylic acid tert-butyl ester

HRID 221375

Reaction equation

HRID 221375 reaction equation
Br.Br[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)=O.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([O:25][CH2:26][C:27](=[S:29])[NH2:28])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>CO.CCOC(C)=O>[C:12]([O:16][C:17]([N:19]1[CH2:20][CH2:21][CH:22]([O:25][CH2:26][C:27]2[S:29][CH:3]=[C:4]([C:6]3[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=3)[N:28]=2)[CH2:23][CH2:24]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 27762394-(Bromoacetyl)pyridine hydrobromideHCID 45496681Tert-butyl 4-(carbamothioylmethoxy)piperidine-1-carboxylate

Product 1

HCID 579544514-(4-Pyridin-4-yl-thiazol-2-ylmethoxy)piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-bromo-1-pyridin-4-yl-ethanone hydrobromide (35 mg, 1241 mol) and 4-thiocarbamoylmethoxypiperidine-1-carboxylic acid tert-butyl ester (Preparation 18, 34 mg, 124 μmol) in methanol (2 ml) was heated at 60° C. for 1.5 h. The reaction mixture was diluted with EtOAc (60 ml), washed with saturated aqueous NaHCO3 (15 ml) and brine (15 ml) then dried (MgSO4). The solvent was removed and the residue purified by flash chromatography (EtOAc) to afford the title compound: RT=2.95 ml, m/z (ES+)=376.1 [M+H]+.

Workup

  1. washwashed with saturated aqueous NaHCO3 (15 ml) and brine (15 ml)
  2. dry with materialthen dried (MgSO4)
  3. customThe solvent was removed
  4. customthe residue purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-af4f12460c324f09932ce5267922013d
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Linked notes

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