2-Chloro-6-(tributylstannyl)pyrazine → HCID 86709767, compound

HRID 1529296Notes

Reaction equation

HRID 1529296 reaction equation
[Cl:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Sn](CCCC)(CCCC)CCCC)[N:3]=1.[F: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]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH:33]=[C:32]2I>CN(C=O)C.C(Cl)Cl.[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:1][C:2]1[N:3]=[C:4]([C:32]2[C:31]3[C:35](=[CH:36][CH:37]=[C:29]([C:23]4[C:24]([F:28])=[CH:25][CH:26]=[CH:27][C:22]=4[F:21])[CH:30]=3)[N:34]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH:33]=2)[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 2

HCID 117740572-Chloro-6-(tributylstannyl)pyrazineHCID 67958266tert-butyl 5-(2,6-difluorophenyl)-3-iodo-1H-indole-1-carboxylate

Product 1

HCID 86709767HCID 86709767, compoundYield 35.1%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A glass microwave reaction vessel was charged with 2-chloro-6-(tributylstannyl)pyrazine (177 mg, 0.439 mmol) and tert-butyl 5-(2,6-difluorophenyl)-3-iodo-1H-indole-1-carboxylate (200 mg, 0.439 mmol) in DMF (2.5 mL) followed by CuI (18 mg, 0.044 mmol) and Pd(PPh3)4 (50.8 mg, 0.044 mmol). The reaction mixture was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 100° C. for 40 min, and then the mixture was diluted with DCM. The organic layer was separated, washed with water (20 mL×4), dried over Na2SO4, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 0-5% EtOAc in Hexanes) to give tert-butyl 3-(6-chloropyrazin-2-yl)-5-(2,6-difluorophenyl)-1H-indole-1-carboxylate (68.0 mg, 0.154 mmol, 35.0% yield) as a white solid. MS (ESI, pos. ion) m/z: 442 (M+1).

Workup

  1. customA glass microwave reaction vessel
  2. customThe organic layer was separated
  3. washwashed with water (20 mL×4)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with silica gel chromatography (eluting with 0-5% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-0614f5687eb045a490754aa523f07600
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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