Allyl bromide → HCID 11626839, compound

HRID 733395Notes

Reaction equation

HRID 733395 reaction equation
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]([CH:9]1[C:22]3[CH:21]=[CH:20][C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[NH:29][C:30](=[O:32])[CH3:31])=[CH:18][C:17]=3[O:16][C:15]3[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:2]2.C(=O)([O-])[O-].[K+].[K+].[CH2:39](Br)[CH:40]=[CH2:41]>CN(C=O)C>[CH2:41]([N:8]1[CH:1]2[CH2:7][CH2:6][CH:5]1[CH2:4][CH:3]([CH:9]1[C:22]3[CH:21]=[CH:20][C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[NH:29][C:30](=[O:32])[CH3:31])=[CH:18][C:17]=3[O:16][C:15]3[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:2]2)[CH:40]=[CH2:39]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 11539108HCID 11539108, compound2×

Product 1

HCID 11626839HCID 11626839, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-{2-[9-(8-Aza-bicyclo[3.2.1]oct-3-yl)-9H-xanthen-3-yl]-phenyl}-acetamide, 7b (53 mg, 0.125 mmol) in DMF (0.5 mL) at 0° C. were added potassium carbonate (18 mg, 0.13 mmol) and allyl bromide (10.6 μL, 0.122 mmol). The mixture was stirred overnight at rt, and poured onto H2O. The solid was separated via filtration and washed with H2O. The solid was purified via reverse phase HPLC (eleuent gradient: 10% to 90% CH3CN in H2O containing 0.1% TFA) to yield 25 mg (36%) of N-{2-[9-(8-allyl-8-aza-bicyclo[3.2.1]oct-3-yl)-9H-xanthen-3-yl]-phenyl}-acetamide, 18b. MS 18b: m/z: 464.9 (MH+).

Workup

  1. additionpoured onto H2O
  2. customThe solid was separated via filtration
  3. washwashed with H2O
  4. customThe solid was purified via reverse phase HPLC (eleuent gradient: 10% to 90% CH3CN in H2O containing 0.1% TFA)

Sources & evidence

ORD record
ord-e0a912064cd74d839e33a00b767549d1
Source dataset
uspto-grants-2009_09
Patent number
US07589104B2

Reaction notes

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