Sodium hydride → 6'-Bromo-1'-(8-chloro-2,3-dimethylquinolin-4-yl)-1',2,2',3,5,6-hexahydrospiro-[pyran-4,3'-pyrrolo[3,2-b]pyridine]

HRID 1618708Notes

Reaction equation

HRID 1618708 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][CH2:9][C:8]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:5]2=[N:6][CH:7]=1.Cl[C:17]1[C:26]2[C:21](=[C:22]([Cl:27])[CH:23]=[CH:24][CH:25]=2)[N:20]=[C:19]([CH3:28])[C:18]=1[CH3:29].[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]([C:17]3[C:26]4[C:21](=[C:22]([Cl:27])[CH:23]=[CH:24][CH:25]=4)[N:20]=[C:19]([CH3:28])[C:18]=3[CH3:29])[CH2:9][C:8]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 596315464,8-Dichloro-2,3-dimethylquinolineHCID 672845606'-Bromo-1',2,2',3,5,6-hexahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridine]

Product 1

HCID 672845186'-Bromo-1'-(8-chloro-2,3-dimethylquinolin-4-yl)-1',2,2',3,5,6-hexahydrospiro-[pyran-4,3'-pyrrolo[3,2-b]pyridine]

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to procedure M by using 6′-bromo-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] (150 mg, 0.56 mmol), 4,8-dichloro-2,3-dimethylquinoline (126 mg, 0.56 mmol) and NaH (48.6 mg, 1.11 mmol, 55% dispersion in oil) in DMF (2.5 mL) while heating the reaction at 60° C. for 14 h. Purification by reverse phase HPLC (10 to 60% acetonitrile in water) gave 6′-bromo-1′-(8-chloro-2,3-dimethylquinolin-4-yl)-1′,2,2′,3,5,6-hexahydrospiro-[pyran-4,3′-pyrrolo[3,2-b]pyridine]. Mass Spectrum (ESI) m/e=458.0 [(M+1) (79Br)] and 460.0 [(M+1) (81Br)].

Workup

  1. customPrepared
  2. temperaturewhile heating
  3. customthe reaction at 60° C. for 14 h
  4. customPurification by reverse phase HPLC (10 to 60% acetonitrile in water)

Sources & evidence

ORD record
ord-164a9b1e4ea94731894f303b0cdd8fd7
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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