Diisopropylethylamine → HCID 64992279, compound

HRID 1393042Notes

Reaction equation

HRID 1393042 reaction equation
BrC1N(C)N=CC=1[C:8](O)=[O:9].[NH:11]1[CH:20]2[CH:15]([CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:14][CH2:13][CH2:12]1.C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl.CN(C)C=O>[N:11]1([CH:8]=[O:9])[CH:20]2[CH:15]([CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 92911DecahydroquinolineHCID 2733179PyBroPHCID 596795725-bromo-1-methyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 64992279HCID 64992279, compoundYield 159.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

5-Bromo-1-methyl-1H-pyrazole-4-carboxylic acid (29.6 mmol), decahydro-quinoline (Aldrich Chemical Company, Inc., Milwaukee, Wis.; 4.9 g, 35.5 mmol), diisopropylethylamine (11 mL, 59.2 mmol), and PyBrop (bromo-tris-pyrrolidino-phophonium hexafluorophosphate) (Chem-Impex International, Inc., Wood Dale, Ill.; 16.6 g, 35.5 mmol) were mixed together in dry dichloromethane (70 mL) and dry dimethylformamide (20 mL). The mixture was stirred overnight at room temperature. At this time, the mixture was diluted with dichloromethane and extracted three times with water. The combined dichloromethane extracts were evaporated, and the residue was purified by flash chromatography, eluting with 0-10% ethyl acetate/hexanes to give 5-bromo-1-methyl-1H-pyrazol-4-yl)-(octahydro-quinolin-1-yl)-methanone (7.9 g, 82% yield).

Workup

  1. extractionextracted three times with water
  2. customThe combined dichloromethane extracts were evaporated
  3. customthe residue was purified by flash chromatography
  4. washeluting with 0-10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0105f06a03784daba6dcb439eec24aef
Source dataset
uspto-grants-2008_03
Patent number
US07345058B2

Reaction notes

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