Dimethylformamide → HCID 68580039, compound

HRID 2233905Notes

Reaction equation

HRID 2233905 reaction equation
Br[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13]2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:26][N:27](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:22]([O:21][C:19]([NH:18][CH:15]1[CH2:16][CH2:17][N:12]([C:4]2[S:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]([C:26]#[N:27])[N:3]=2)[CH2:13][CH2:14]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 68579949HCID 68579949, compound2×

Product 1

HCID 68580039HCID 68580039, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Procedure

A solution of ethyl 4-bromo-2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1,3-thiazole-5-carboxylate (Intermediate 222) (1.3 g, 2.9 mmol), Zn(CN)2 (250 mg, 2.2 mmol), tris(dibenzylidineaceetone)dipalladium(0) (125 mg, 0.13 mmol) and 1,1′-bis(diphenylphosphino) ferrocene (151 mg, 13 mmol) in 20 ml DMF under argon was heated at 130° C. for 1 hour in a microwave reactor. Solvent was removed and the residue was taken up in EtOAc and washed with water and brine. Drying (MgSO4) and removal of solvent gave an oil that was chromatographed on silica gel (DCM followed by gradient elution to 5% MeOH in DCM) to give 1.9 g of product as a yellow solid.

Workup

  1. customSolvent was removed
  2. washwashed with water and brine
  3. customDrying
  4. custom(MgSO4) and removal of solvent
  5. customgave an oil that
  6. customwas chromatographed on silica gel (DCM followed by gradient elution to 5% MeOH in DCM)

Sources & evidence

ORD record
ord-14f19b3b64624719ae21e2b78cbb93cf
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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