Cesium carbonate → HCID 67958593, compound

HRID 1529338Notes

Reaction equation

HRID 1529338 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](I)[CH:7]=1.[NH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(C1CCCCC1=O)(=O)C(C)C>CCOC(C)=O.O1CCOCC1>[Br:1][C:2]1[CH:7]=[C:6]([NH:9][CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:5]=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 5458091-BOC-3-AminopiperidineHCID 8204093-Bromo-5-iodopyridineHCID 114693012-(2-Methylpropanoyl)cyclohexan-1-one

Product 1

HCID 67958593HCID 67958593, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3-bromo-5-iodopyridine (500 mg, 1.761 mmol, Aldrich), tert-butyl 3-aminopiperidine-1-carboxylate (388 mg, 1.937 mmol, Combi-blocks), Cut (33.5 mg, 0.176 mmol, Aldrich) and cesium carbonate (1148 mg, 3.52 mmol, Fluka) was capped, degassed and backfilled with argon (3×). Dioxane (2 mL) and 2-isobutyrylcyclohexanone (0.118 mL, 0.704 mmol) were added, and the reaction was heated to 55° C. After 16 h, the temperature was raised to 70° C. After 60 h at 70° C., the reaction mixture was cooled to 23° C., diluted with EtOAc (75 mL) and washed with brine (50 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluent: 25-60% EtOAc/hexane), affording tert-butyl 3-(5-bromopyridin-3-ylamino)piperidine-1-carboxylate (375 mg, 60%). MS (ESI, pos. ion) m/z: 356.1 (M+1), 358.1 (M+3).

Workup

  1. customwas capped
  2. customdegassed
  3. temperaturethe temperature was raised to 70° C
  4. waitAfter 60 h at 70° C.
  5. temperaturethe reaction mixture was cooled to 23° C.
  6. washwashed with brine (50 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. custompurified by silica gel chromatography (eluent: 25-60% EtOAc/hexane)

Sources & evidence

ORD record
ord-e7b0b0cfbe6e43f3a716d6f3afa0f69b
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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