1H-Pyrrolo(2,3-b)pyridine → HCID 178454099, compound

HRID 707379Notes

Reaction equation

HRID 707379 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[H-].[Na+].CS(O[C@H:17]1[CH2:20][C@@H:19]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]1)(=O)=O>CN(C=O)C>[C:25]([O:24][C:22](=[O:23])[NH:21][C@H:19]1[CH2:18][C@H:17]([N:1]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[CH:3]=[CH:2]2)[CH2:20]1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 24758Sodium hydrideHCID 178454135HCID 178454135, compound

Product 1

HCID 178454099HCID 178454099, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1H-pyrrolo[2,3-b]pyridine (44.5 mg, 0.377 mmol) in DMF (1.3 ml) at room temperature was added sodium hydride, 60% in oil (18 mg, 0.45 mmol), followed by cis-3-((tert-butoxycarbonyl)amino)cyclobutyl methanesulfonate (100 mg, 0.38 mmol). The reaction mixture was heated at 100° C. for 16 h. The reaction mixture was partitioned between EtOAc and water. The aqueous layer was back extracted with EtOAc (2×) and the combined organics was dried (MgSO4) and concentrated. The crude product was purified by ISCO (12 g), eluting with a gradient of EtOAc/hexane 0-50% to provide tert-butyl(trans-3-(1H-pyrrolo[2,3-b]pyridin-1-yl)cyclobutyl)carbamate (10 mg, 0.035 mmol, 9.23% yield) as off-white solid. ESI (M+1) 288.0.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. extractionThe aqueous layer was back extracted with EtOAc (2×)
  3. dry with materialthe combined organics was dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by ISCO (12 g)
  6. washeluting with a gradient of EtOAc/hexane 0-50%

Sources & evidence

ORD record
ord-f83837ff95a5483b8d3391a9a5f8811f
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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