2-Bromopropane → HCID 10499786, compound

HRID 1172277Notes

Reaction equation

HRID 1172277 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][N:18]=2)=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH:28](Br)([CH3:30])[CH3:29]>CN(C=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH:28]([CH3:30])[CH3:29])[N:18]=2)=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 10568741HCID 10568741, compound

Product 1

HCID 10499786HCID 10499786, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(1-benzylpiperidin-4-yl)-indazole-3-carboxamide (3.34 g, 10.0 mmol) in dry DMF (70 ml) under argon atmosphere was added sodium hydride (0.25 g, 10.0 mmol) and stirred at room temperature for 3 h. The mixture was added isopropylbromide (1.37 g, 11.0 mmol) and stirred for additional 24 h. The reaction mixture was evaporated in vacuo and the residue added EtOAc (100 ml). The organic layer washed with brine (50 ml) and H2O (2×50 ml). The organic layer was dried over Na2SO4, filtered and evaporated in vacuo to leave an oil that solidified upon standing. The oil was separated with flash chromatography (SiO2, Et2O/Hexane (2:1) to leave the product as a solid (1.22 g, 32.7%).

Workup

  1. stirringstirred for additional 24 h
  2. customThe reaction mixture was evaporated in vacuo
  3. additionthe residue added EtOAc (100 ml)
  4. washThe organic layer washed with brine (50 ml) and H2O (2×50 ml)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto leave an oil that
  9. customThe oil was separated with flash chromatography (SiO2, Et2O/Hexane (2:1)

Sources & evidence

ORD record
ord-8e33c424223645b1b59973793f5fee92
Source dataset
uspto-grants-2010_11
Patent number
US07834010B2

Reaction notes

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