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2-Chloro-6-(tributylstannyl)pyrazine → 5-(2-chloro-6-fluorophenyl)-3-(6-chloropyrazin-2-yl)-1-tosyl-1H-indole

HRID 1529318
Notes
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Reaction equation

HRID 1529318 reaction equation
[Cl:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Sn](CCCC)(CCCC)CCCC)[N:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[N:34]([S:38]([C:41]1[CH:47]=[CH:46][C:44]([CH3:45])=[CH:43][CH:42]=1)(=[O:40])=[O:39])[CH:33]=[C:32]2I>CN(C=O)C.[Cu]I.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>[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[N:34]([S:38]([C:41]1[CH:42]=[CH:43][C:44]([CH3:45])=[CH:46][CH:47]=1)(=[O:39])=[O:40])[CH:33]=[C:32]2[C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Cl:1])[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 117740572-Chloro-6-(tributylstannyl)pyrazineHCID 679597685-(2-chloro-6-fluorophenyl)-3-iodo-1-tosyl-1H-indole

Product 1

HCID 867097705-(2-chloro-6-fluorophenyl)-3-(6-chloropyrazin-2-yl)-1-tosyl-1H-indoleYield 91%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 178418397
HCID 178418397, compound
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

Argon was bubbled through a slurry of CuI (0.036 g, 0.190 mmol), Pd(PPh3)4 (0.110 g, 0.095 mmol), 2-chloro-6-(tributylstannyl)pyrazine (1.151 g, 2.85 mmol), 5-(2-chloro-6-fluorophenyl)-3-iodo-1-tosyl-1H-indole (1.00 g, 1.902 mmol) in 9 mL DMF for 2 min. The reaction was sealed and heated to 105° C. for 2 h. The reaction was cooled and partitioned between EtOAc and water. The organic layer was washed 1× brine, dried over Na2SO4, filtered, and concentrated in vacuo. The material was treated with DCM and purified by silica gel chromatography (80 g column) using 0-30% EtOAc/hexane. The product-containing fractions were concentrated to afford 5-(2-chloro-6-fluorophenyl)-3-(6-chloropyrazin-2-yl)-1-tosyl-1H-indole (0.88 g, 1.72 mmol, 91% yield) as a light-yellow solid. MS (ESI, pos. ion) m/z: 512 (M+1).

Workup

  1. customThe reaction was sealed
  2. temperatureThe reaction was cooled
  3. custompartitioned between EtOAc and water
  4. washThe organic layer was washed 1× brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. additionThe material was treated with DCM
  9. custompurified by silica gel chromatography (80 g column)
  10. concentrationThe product-containing fractions were concentrated

Sources & evidence

ORD record
ord-b9decbc746d648e0a37ba62156bc032f
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09090593B2

Reaction notes

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