2-Bromoethanol → HCID 67435435, compound

HRID 1663396Notes

Reaction equation

HRID 1663396 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:19]2[C:28]3[C:27](=[O:29])[CH2:26][CH:25]([CH2:30][CH2:31][CH3:32])[CH2:24][C:23]=3[NH:22][C:21]([CH3:33])=[C:20]2[C:34]#[N:35])[CH:5]=[C:6]([OH:18])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1.Br[CH2:37][CH2:38][OH:39].C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:19]2[C:28]3[C:27](=[O:29])[CH2:26][CH:25]([CH2:30][CH2:31][CH3:32])[CH2:24][C:23]=3[NH:22][C:21]([CH3:33])=[C:20]2[C:34]#[N:35])[CH:5]=[C:6]([O:18][CH2:37][CH2:38][OH:39])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1

Participants

7

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 67435389HCID 67435389, compound

Product 1

HCID 67435435HCID 67435435, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-[3-bromo-5-hydroxy-4-(3-methoxy-benzyloxy)-phenyl]-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile (100 mg), 2-bromoethanol (16 μl), tetrabutylammonium iodide (5 mg) and potassium carbonate (50 mg) in DMF (2 ml) was stirred at 70° C. for 17 h. The mixture was diluted with ethyl acetate and washed with water. The organic layer was dried (MgSO4), filtered and concentrated in vacuo.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64806c67ffbe4048b7837dbf1f90c4f9
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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