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2-(Tributylstannyl)pyrazine → HCID 58579508, compound

HRID 1662212
Notes
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Reaction equation

HRID 1662212 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:10]2([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:18]3[C:13](=[C:14]([F:19])[CH:15]=[CH:16][CH:17]=3)[C:12]([NH2:20])=[N:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C([Sn](CCCC)(CCCC)[C:36]1[CH:41]=[N:40][CH:39]=[CH:38][N:37]=1)CCC>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.CN(C=O)C>[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[C:12]([NH2:20])=[N:11][C:10]2([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([C:36]2[CH:41]=[N:40][CH:39]=[CH:38][N:37]=2)[CH:3]=1)[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 27373162-(Tributylstannyl)pyrazineHCID 58579532HCID 58579532, compound

Product 1

HCID 58579508HCID 58579508, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228Dimethylformamide
Solvent

Procedure

1-(3-Bromo-4-methoxyphenyl)-4-fluoro-1-(2-(trifluoromethyl)pyridin-4-yl)-1H-isoindol-3-amine (1.5 g, 3.12 mmol), 2-tributylstannylpyrazine (1.268 g, 3.44 mmol), tetrakis(triphenylphosphine)palladium(0) (0.361 g, 0.31 mmol) and DMF (10 mL) were heated in a microwave oven for 20 min at 150° C. The reaction mixture was filtered and concentrated under reduced pressure. The residue was diluted with DCM (40 ml) and silica powder was added and the mixture was concentrated under reduced pressure. The residue was purified by flash column chromatography (0-10% 0.1M NH3 in Methanol in DCM) to afford the title compound (0.82 g, 54.8%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with DCM (40 ml) and silica powder
  4. additionwas added
  5. concentrationthe mixture was concentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography (0-10% 0.1M NH3 in Methanol in DCM)

Sources & evidence

ORD record
ord-e60b6049b694442d881018d3313c9276
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08030500B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes