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Ammonia → HCID 19962765, compound

HRID 52012
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Reaction equation

HRID 52012 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:20]=[CH:19][C:18]3[NH:17][C:16]([CH3:21])=[CH:15][C:14]=3[C:13]=2[C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[N:4]=1.S1(CCCC1)(=O)=O.F[B-](F)(F)F.[O:40]=[N+:41]=[O:42].N>C(#N)C>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C:12]2[CH:20]=[CH:19][C:18]3[NH:17][C:16]([CH3:21])=[C:15]([N+:41]([O-:42])=[O:40])[C:14]=3[C:13]=2[C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[N:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 222AmmoniaHCID 31347SulfolaneHCID 11073463Nitronium tetrafluoroborateHCID 19962801Allyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate

Product 1

HCID 19962765HCID 19962765, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
-30 °C

Procedure

2.0 g of allyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate was dissolved in 25 ml of acetonitrile, and the solution was cooled to -30° C. 16.3 ml of a 0.5M sulfolane solution of nitronium tetrafluoroborate was dropwise added thereto, and the mixture was stirred for 5 hours. After adding 2 ml of aqueous ammonia, the mixture was returned to room temperature and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Crystals obtained by concentration under reduced pressure, were washed with hexane to obtain 1.23 g (yield: 55%) of the desired compound.

Workup

  1. customwas returned to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customCrystals obtained by concentration under reduced pressure
  6. washwere washed with hexane

Sources & evidence

ORD record
ord-db6c76928253418dbbd275443d117cd1
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05616537

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes