Sodium hydride → HCID 58127262, compound

HRID 1623248Notes

Reaction equation

HRID 1623248 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:4][C:3]=1[Cl:16].[H-].[Na+].CC1C=CC(S(O[CH2:30][C:31]2([O:37][CH3:38])[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)(=O)=O)=CC=1>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]([N:8]([CH2:30][C:31]2([O:37][CH3:38])[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH:5]=[CH:4][C:3]=1[Cl:16]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 58127128(4-methoxytetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate2×HCID 86650605HCID 86650605, compound

Product 1

HCID 58127262HCID 58127262, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of tert-butyl 6-bromo-5-chloropyridin-2-ylcarbamate (140 mg, 0.455 mmol) in DMF (2 ml) under nitrogen was added NaH (60%, 30 mg, 0.774 mmol). The resulting mixture was stirred at ambient temperature for one hour. A solution of (4-methoxytetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate (intermediate O, 164 mg, 0.546 mmol) in DMF (1.5 ml) was then added to the preceding mixture. The resulting mixture was then stirred overnight at about 85° C. The stirred mixture was diluted with 30 ml of ethyl acetate, washed with water (20 ml×3) and dried. After concentration the resulting residue was purified by silica gel chromatography using a 12 g column, eluting with 5-20% ethyl acetate in hexane to yield the desired compound “P” as a viscous oil (92 mg), which solidified upon standing overnight. LCMS (m/z): 437.0 [M+H]+; Retention time=1.158 min.

Workup

  1. stirringThe resulting mixture was then stirred overnight at about 85° C
  2. washwashed with water (20 ml×3)
  3. customdried
  4. concentrationAfter concentration the resulting residue
  5. customwas purified by silica gel chromatography
  6. washeluting with 5-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c361e91e953b4d4abd51d4a73d777fab
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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