Toluene → HCID 58204350, compound

HRID 1498074Notes

Reaction equation

HRID 1498074 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]

Participants

5

Reactant 3

HCID 1140TolueneHCID 179620285-amino-1-isopropyl-1H-pyrazole-4-carbonitrileHCID 58205021HCID 58205021, compound

Product 1

HCID 58204350HCID 58204350, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

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-b0e6fcd439cb4eeeb44759c28925fdf9
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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