Diisopropylethylamine → HCID 58924815, compound

HRID 1990996Notes

Reaction equation

HRID 1990996 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.[NH:10]1[CH:19]2[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18]2)[CH2:13][CH2:12][CH2:11]1.CCN(C(C)C)C(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([N:10]2[CH:19]3[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18]3)[CH2:13][CH2:12][CH2:11]2)=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 92911DecahydroquinolineHCID 2733179PyBroPHCID 27632092-Bromo-1,3-thiazole-4-carboxylic acid2×

Product 1

HCID 58924815HCID 58924815, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-bromo-thiazole-4-carboxylic acid (Intermediate 3; 21.2 mmol), decahydroquinoline (3.54 g, 25.4 mmol), DIPEA (7.4 mL, 42.4 mmol), and PyBrop (11.9 g, 25.4 mmol) in dry DCM (70 mL) was stirred overnight at room temperature. The mixture was extracted with DCM and water three times. The combined DCM extracts were evaporated, and the residue was chromatographed on silica, eluting with EtOAc/Hexane (0-10% gradient) to give (2-bromo-thiazol-4-yl)-(octahydro-quinolin-1-yl)-methanone (6.0 g, 86%).

Workup

  1. extractionThe mixture was extracted with DCM and water three times
  2. customThe combined DCM extracts were evaporated
  3. customthe residue was chromatographed on silica
  4. washeluting with EtOAc/Hexane (0-10% gradient)

Sources & evidence

ORD record
ord-3fa3258abb2c49e39c6315a0ebe97abb
Source dataset
uspto-grants-2010_01
Patent number
US07645773B2

Reaction notes

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