Sodium hydride → HCID 118598676, compound

HRID 1050421Notes

Reaction equation

HRID 1050421 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[C:9](=[O:21])[N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH2:11][C:4]=12.[H-].[Na+].FC(F)CN1[CH2:32][CH2:31][C:30]2(N3C(=O)C(NC4N=CN=C(NC(C5CC5)=O)C=4OC)=CC(C)=C3C(=O)N2)[CH2:29][CH2:28]1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[C:9](=[O:21])[N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:11]3([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[C:4]=12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 118598750HCID 118598750, compoundHCID 118598928HCID 118598928, compound

Product 1

HCID 118598676HCID 118598676, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methoxy-6-(4-methoxybenzyl)-5,6-dihydro-7H-pyrrolo[3,4-b]pyridin-7-one (2, 1.0 mmol, 1 eq) in tetrahydrofuran (25 mL) add sodium hydride (2.5 mmol, 2.5 eq) at 0° C. Stir the mixture for 20 min and then add 1,5-dibromo pentane (3, 1.5 mmol, 1.5 eq) and stir for 8 h. After completion quench the mixture with water at 0° C. and add ethyl acetate. Separate the layer and remove the solvent to get crude. Purify the crude by silica gel column chromatography to afford 4′-methoxy-6′-(4-methoxybenzyl)spiro[cyclohexane-1,5′-pyrrolo[3,4-b]pyridin]-7′(6′H)-one (4).

Workup

  1. customAfter completion quench the mixture with water at 0° C.
  2. additionadd ethyl acetate
  3. customSeparate the layer
  4. customremove the solvent
  5. customto get crude
  6. customPurify the crude by silica gel column chromatography

Sources & evidence

ORD record
ord-df9a2d82b7ae4c5d9903431409801238
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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