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Toluene → HCID 58204350, compound

HRID 1530393
Notes
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Reaction equation

HRID 1530393 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[N:7]=[C:8]2[C:14]3[CH:15]=[CH:16][C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:18][C:13]=3[O:12][CH2:11][CH2:10][N:9]2[CH:23]=1)CCC.N[C:33]1[N:37]([CH:38]([CH3:40])[CH3:39])[N:36]=[CH:35][C:34]=1[C:41]#[N:42].C1(C)C=CC=CC=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>[C:41]([C:34]1[CH:35]=[N:36][N:37]([CH:38]([CH3:40])[CH3:39])[C:33]=1[C:6]1[N:7]=[C:8]2[C:14]3[CH:15]=[CH:16][C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:18][C:13]=3[O:12][CH2:11][CH2:10][N:9]2[CH:23]=1)#[N:42]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1140TolueneHCID 179620285-amino-1-isopropyl-1H-pyrazole-4-carbonitrileHCID 58205021Methyl 2-(tributylstannyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylate

Product 1

HCID 58204350HCID 58204350, compound

Reagents, catalysts & solvents 1

HCID 178418397
HCID 178418397, compound
Catalyst

Procedure

A mixture of methyl 2-(tributylstannyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylate (155 mg, 0.291 mmol), 5-amino-1-isopropyl-1H-pyrazole-4-carbonitrile (133 mg, 0.509 mmol) and Tetrakis(triphenylphosphine)palladium(0) (16.8 mg, 0.0145 mmol) in Toluene (6.0 mL, 56 mmol) was heated for 18 hours. The mixture was concentrated in vacuum, the residue purified on 4 g silica column eluting with 30% ethyl acetate in heptane. Yield 65 mg (59%). MS (ESI+): 378.2

Workup

  1. temperaturewas heated for 18 hours
  2. concentrationThe mixture was concentrated in vacuum
  3. customthe residue purified on 4 g silica column
  4. washeluting with 30% ethyl acetate in heptane

Sources & evidence

ORD record
ord-c67d8a86f9394e2f8839049b89433f3d
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09090628B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes