Water → 8-(5-Bromo-4-(4-chlorophenyl)thiazol-2-yl)-3-oxa-8-azabicyclo[3.2.1]octane

HRID 1051888Notes

Reaction equation

HRID 1051888 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:13]3[CH:18]4[CH2:19][CH2:20][CH:14]3[CH2:15][O:16][CH2:17]4)[S:11][CH:12]=2)=[CH:4][CH:3]=1.[Br:21]N1C(=O)CCC1=O.O.[OH-].[Na+]>CN(C=O)C>[Br:21][C:12]1[S:11][C:10]([N:13]2[CH:18]3[CH2:19][CH2:20][CH:14]2[CH2:15][O:16][CH2:17]3)=[N:9][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 898133778-(4-(4-Chlorophenyl)thiazol-2-yl)-3-oxa-8-azabicyclo[3.2.1]octane2×

Product 1

HCID 898133608-(5-Bromo-4-(4-chlorophenyl)thiazol-2-yl)-3-oxa-8-azabicyclo[3.2.1]octaneYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 8-(4-(4-chlorophenyl)thiazol-2-yl)-3-oxa-8-azabicyclo[3.2.1]octane (Step-2 of compound 56, 0.27 g, 0.88 mmol) in DMF (5 ml) at 0° C. was added N-bromosuccinimide (0.19 g, 1.06 mmol) in a portion wise manner. The resulting mixture was stirred at room temperature for 30 min. The progress of reaction was monitored by TLC. To the reaction mixture water (20 ml) and 1M NaOH solution (5 ml) were added slowly and aqueous layer was extracted with ethyl acetate (2×30 ml). The reaction mixture was washed with water (1×20 ml). The combined organic layer was dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure to obtain a crude product; which was purified by flash column chromatography using 10% ethyl acetate in hexanes as an eluent to obtain the title compound (0.26 g, 78.0%). MS: m/z 386 (M+1).

Workup

  1. customThe progress of reaction
  2. extractionaqueous layer was extracted with ethyl acetate (2×30 ml)
  3. washThe reaction mixture was washed with water (1×20 ml)
  4. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  5. customthe solvent was evaporated under reduced pressure
  6. customto obtain a crude product
  7. customwhich was purified by flash column chromatography

Sources & evidence

ORD record
ord-73b42c4bf7b948ca9e129669a8a0d8ae
Source dataset
uspto-grants-2016_07
Patent number
US09388196B2

Reaction notes

Loading…