Sodium hydride → HCID 59394157, compound

HRID 45171Notes

Reaction equation

HRID 45171 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:16]=[CH:15][N:14]=[C:13]([CH2:17][N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:12]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH:27]1([C:30]2[N:34]([CH3:35])[N:33]=[C:32]([NH:36][C:37](=O)[O:38]C3C=CC=CC=3)[CH:31]=2)[CH2:29][CH2:28]1.[H-].[Na+]>CN(C=O)C>[CH:27]1([C:30]2[N:34]([CH3:35])[N:33]=[C:32]([NH:36][C:37]([N:1]3[C:9]4[C:4](=[CH:5][C:6]([O:10][C:11]5[CH:16]=[CH:15][N:14]=[C:13]([CH2:17][N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH:12]=5)=[CH:7][CH:8]=4)[CH:3]=[CH:2]3)=[O:38])[CH:31]=2)[CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 59394356HCID 59394356, compoundHCID 59394376HCID 59394376, compound

Product 1

HCID 59394157HCID 59394157, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (4-(1H-indol-5-yloxy)pyridin-2-yl)methyl(methyl)carbamate (115 mg, 0.325 mmol), in DMF (5 ml) is added phenyl 5-cyclopropyl-1-methyl-1H-pyrazol-3-ylcarbamate (126 mg, 0.488 mmol), prepared as described in Example 5-N. The resulting mixture is placed at 0° C. and sodium hydride (60% dispersion in oil; 39.0 mg, 0.98 mmol) is added. The reaction is permitted to stir at 0° C. for 30 min at which time the reaction is quenched with saturated aqueous NH4Cl. The resulting mixture is diluted with brine and DCM. The resulting layers are separated and the aqueous layer is extracted twice with DCM. The organic layers are combined, dried over anhydrous Na2SO4, filtered, and concentrated. The resulting residue is purified via FCC (0-100% EtOAc/heptane) to give the title compound. MS (ESI) m/z 517.6 (M+1).

Workup

  1. customprepared
  2. customis placed at 0° C.
  3. customis quenched with saturated aqueous NH4Cl
  4. additionThe resulting mixture is diluted with brine and DCM
  5. customThe resulting layers are separated
  6. extractionthe aqueous layer is extracted twice with DCM
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting residue is purified via FCC (0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-473eed8cb8994d1ba34437b74a2c5f4d
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Reaction notes

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