Bromine → HCID 10021468, compound

HRID 2220128Notes

Reaction equation

HRID 2220128 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]3[CH2:14][C@:13]4([CH:19]5[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]5)[CH2:15]4)[O:12][C:9]3=[N:10][CH:11]=2)=[CH:2]1.[Br:22]Br>CN(C=O)C.C(Cl)(Cl)Cl>[Br:22][C:2]1[O:1][CH:5]=[CH:4][C:3]=1[C:6]1[CH:7]=[C:8]2[CH2:14][C@:13]3([CH:19]4[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]4)[CH2:15]3)[O:12][C:9]2=[N:10][CH:11]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 9860561HCID 9860561, compound

Product 1

HCID 10021468HCID 10021468, compoundYield 20.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

(2′R)-5′-(Furan-3-yl)spiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (102 mg, 0.37 mmol), was stirred with bromine (65 mg, 0.41 mmol) in DMF (3 ml) at room temperature for 1 h. Vaccum was applied, and the mixture was stirred for a further 30 min. The reaction mixture was diluted with chloroform, and washed with aqueous sodium hydroxide, then the organic layer was dried, filtered and evaporated. The compound was purified by flash chromatography using a gradient of ammoniated methanol in chloroform to give the title compound (28 mg) as a pale solid; m/z 361, 363 (MH+).

Workup

  1. washwashed with aqueous sodium hydroxide
  2. customthe organic layer was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe compound was purified by flash chromatography

Sources & evidence

ORD record
ord-ccd49b67d6dc4460af1f87f02331dbcd
Source dataset
uspto-grants-2008_08
Patent number
US07417049B2

Reaction notes

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