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Potassium Phosphate, Tribasic → HCID 86630875, compound

HRID 17553
Notes
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Reaction equation

HRID 17553 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[NH2:9][C:10]1[C:17]([N+:18]([O-:20])=[O:19])=[C:16]([N:21]2[CH2:25][CH2:24][C@H:23]([N:26]([CH3:28])[CH3:27])[CH2:22]2)[C:15](Br)=[C:14]([CH3:30])[C:11]=1[C:12]#[N:13].[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[NH2:9][C:10]1[C:17]([N+:18]([O-:20])=[O:19])=[C:16]([N:21]2[CH2:25][CH2:24][C@H:23]([N:26]([CH3:28])[CH3:27])[CH2:22]2)[C:15]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:14]([CH3:30])[C:11]=1[C:12]#[N:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 866308742-Amino-5-bromo-4-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-methyl-3-nitrobenzonitrile

Product 1

HCID 86630875HCID 86630875, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 312751,4-DioxaneSolvent

Procedure

Potassium phosphate (115 mg, 0.54 mmol) and Pd(PPh3)4 (16 mg, 5 mol %) were added to a dioxane (3 ml) solution of 2-amino-5-bromo-4-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-methyl-3-nitrobenzonitrile (I-267) (100 mg, 0.27 mmol) and phenylboronic acid (40 mg, 0.33 mmol), followed by purging with nitrogen and heating under reflux for 18 hours. After cooling, water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the residue was subjected to column chromatography, and eluted with a mixed solvent of chloroform/methanol (2:1, v/v) to obtain the entitled compound (89 mg, 90%) as a dark red solid.

Workup

  1. customby purging with nitrogen
  2. temperatureheating
  3. temperatureunder reflux for 18 hours
  4. temperatureAfter cooling
  5. additionwater was added
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated away under reduced pressure
  10. washeluted with a mixed solvent of chloroform/methanol (2:1

Sources & evidence

ORD record
ord-84f4ddda690b40b8a02f0582e27a5e7a
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737166B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes