1,4-Dibromobutane → HCID 178431629, compound

HRID 1269997Notes

Reaction equation

[CH3:1][C:2]1[C:10]([O:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([NH2:18])[CH2:14][CH2:13]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1.Br[CH2:26][CH2:27][CH2:28][CH2:29]Br.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CN(C)C(=O)C>[CH3:1][C:2]1[C:10]([O:11][C@H:12]2[CH2:13][CH2:14][C@H:15]([N:18]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:16][CH2:17]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of trans-4-[(4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)oxy]cyclohexylamine (106 mg, 0.321 mmol), 1,4-dibromobutane (69.3 mg, 0.321 mmol), potassium carbonate (110 mg, 0.80 mmol) and N,N-dimethylacetamide (2.0 ml) was stirred at 80° C. for 2 hours. A 1N-aqueous sodium hydroxide solution (20 ml) was added to the reaction solution, followed by extraction with chloroform (20 ml) (twice). The extract solution was dried over magnesium sulfate and then concentrated to dryness, and the residue oil was purified by elution by a silica gel column chromatography (hexane/ethyl acetate=1:2→hexane/ethyl acetate/triethylamine=20:40:3) to obtain 4-methyl-5-[(trans-4-pyrrolidin-1-ylcyclohexyl)oxy]-1-tetrahydro-2H-pyran-2-yl-1H-indazole (67.1 mg, 55%).

Workup

extractionfollowed by extraction with chloroform (20 ml) (twice)
dry with materialThe extract solution was dried over magnesium sulfate
concentrationconcentrated to dryness
customthe residue oil was purified by elution by a silica gel column chromatography (hexane/ethyl acetate=1:2→hexane/ethyl acetate/triethylamine=20:40:3)

Sources & evidence

ORD record: ord-b91a52945ea44bc68da030e7b1ba31a8
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199147B2

Reaction notes

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