Potassium Iodide → HCID 67438988, compound

HRID 335867

Reaction equation

HRID 335867 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@@:5]2([N:27]=1)[C:18]1[C:17]([Br:19])=[C:16]([OH:20])[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[CH:9][CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].CN(C=O)C.Br[CH2:42][C:43]1([CH3:47])[CH2:46][O:45][CH2:44]1>O.C(OCC)(=O)C>[Br:19][C:17]1[C:18]2[C@:5]3([CH2:4][O:3][C:2]([NH2:1])=[N:27]3)[C:6]3[C:11](=[CH:10][CH:9]=[C:8]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[CH:7]=3)[O:12][C:13]=2[CH:14]=[CH:15][C:16]=1[O:20][CH2:42][C:43]1([CH3:47])[CH2:46][O:45][CH2:44]1

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 144860Oxetane, 3-(bromomethyl)-3-methyl-HCID 58466223(S)-2-amino-1'-bromo-7'-(pyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthen]-2'-ol

Product 1

HCID 67438988HCID 67438988, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a slurry of (S)-2-amino-1′-bromo-7′-(pyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthen]-2′-ol (710 mg, 1.674 mmol), cesium carbonate (1091 mg, 3.35 mmol) and potassium iodide (306 mg, 1.841 mmol) in DMF (6694 μL, 1.674 mmol) at 0° C. was added 3-(bromomethyl)-3-methyloxetane (304 mg, 1.841 mmol). The reaction was removed from the ice bath and allowed to warm to rt. Reaction was allowed to stir at rt overnight before being diluted with water (250 mL) and poured into a separatory funnel containing ethyl acetate (100 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide a red oil that was purified by silica gel chromatography (Redi-Sep pre-packed silica gel column (40 g), 0-100% CH2Cl2 to 10:1 methanol in methylenechloride with 0.1% ammonium hydroxide) to provide (S)-1′-bromo-2′-((3-methyloxetan-3-yl)methoxy)-7′-(pyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine as an off white solid. MS m/z=508.0 [M+H].

Workup

  1. customThe reaction was removed from the ice bath
  2. customReaction
  3. additionpoured into a separatory funnel
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto provide a red oil that
  11. customwas purified by silica gel chromatography (Redi-Sep pre-packed silica gel column (40 g), 0-100% CH2Cl2 to 10:1 methanol in methylenechloride with 0.1% ammonium hydroxide)

Sources & evidence

ORD record
ord-44db42f9fb184262906a595d542d549a
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Linked notes

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