Nitrogen → HCID 136184199, compound

HRID 1043835Notes

Reaction equation

HRID 1043835 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[C:17]([CH2:20][N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH:18]=[CH:19][C:12]2=[N:11][C:10]=1[C:27]1[O:28][C:29]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)=[N:30][N:31]=1)C1C=CC=CC=1.[Si](I)(C)(C)C.N#N.[OH-].[Na+]>C(#N)C.O.CO>[F:39][C:36]1[CH:37]=[CH:38][C:33]([CH2:32][C:29]2[O:28][C:27]([C:10]3[N:11]=[C:12]4[CH:19]=[CH:18][C:17]([CH2:20][N:21]5[CH2:22][CH2:23][O:24][CH2:25][CH2:26]5)=[CH:16][N:13]4[C:14](=[O:15])[C:9]=3[OH:8])=[N:31][N:30]=2)=[CH:34][CH:35]=1

Participants

8

Reactant 4

HCID 947NitrogenHCID 14798Sodium HydroxideHCID 85247Trimethylsilyl iodideHCID 58148021HCID 58148021, compound

Product 1

HCID 136184199HCID 136184199, compoundYield 63.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of the product of example 17 (34 mg, 0.065 mmol) in acetonitrile (7 ml), TMSI (0.08 ml, 0.516 mmol) was added dropwise in the presence of N2 at room temperature and then stirred at room temperature for 2 hours. Methanol (5 ml) was added to quench the reaction. Then the mixture was poured into water (15 ml) and 0.5 N sodium hydroxide solution was added dropwise to adjust the pH 8-9. The mixture was extracted with dichloromethane three times. The combined extracts were washed with aqueous sodium bisulfite and water, dried over anhydrous sodium sulfate and evaporated into dryness. The residue was recrystallized for a mixed solvent of DCM/PE to give the titled product (18 mg, 63.8%). 1H NMR (300 MHz, DMSO-d6) δ 2.43 (t, J=4.5 Hz, 4H), 3.54-3.62 (m, 6H), 4.43 (s, 2H), 7.16-7.25 (m, 2H), 7.39-7.46 (m, 2H), 7.59-7.68 (m, 2H), 8.66 (s, 1H), 10.55 (brs, 1H).

Workup

  1. customto quench
  2. customthe reaction
  3. additionwas added dropwise
  4. extractionThe mixture was extracted with dichloromethane three times
  5. washThe combined extracts were washed with aqueous sodium bisulfite and water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated into dryness
  8. customThe residue was recrystallized for a mixed solvent of DCM/PE

Sources & evidence

ORD record
ord-54fc34f1d11845caa75abfe52030e462
Source dataset
uspto-grants-2013_10
Patent number
US08563562B2

Reaction notes

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