HCID 67959759, compound → HCID 67959959, compound

HRID 1529363Notes

Reaction equation

HRID 1529363 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:27]1[N:32]=[C:31]([N:33]2[CH2:38][CH2:37][CH:36]([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH2:35][CH2:34]2)[CH:30]=[N:29][CH:28]=1)CCC>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>[C:42]([O:41][C:40]([NH:39][CH:36]1[CH2:37][CH2:38][N:33]([C:31]2[N:32]=[C:27]([C:2]3[C:10]4[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=4)[N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:3]=3)[CH:28]=[N:29][CH:30]=2)[CH2:34][CH2:35]1)=[O:46])([CH3:45])([CH3:43])[CH3:44]

Participants

6

Reactant 2

HCID 67959759HCID 67959759, compoundHCID 86709776HCID 86709776, compound

Product 1

HCID 67959959HCID 67959959, compoundYield 30.3%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
90 °C

Procedure

A mixture of 1-tert-butyl 5-methyl 3-iodo-1H-indole-1,5-dicarboxylate (6 g, 14.96 mmol) and tert-butyl 1-(6-(tributylstannyl)pyrazin-2-yl)piperidin-4-ylcarbamate (1d) (10.2 g, 17.95 mmol) in DMF (60 mL) was purged with argon gas for 5 min, added CuI (4.27 g, 22.44 mmol), palladium tetrakis (1.7 g, 1.5 mmol) and again purged with argon gas for 5 min. The reaction mixture was stirred at 90° C. under nitrogen atmosphere for 1 h. The reaction mixture was then poured into water. The resulting precipitate was collected by filtration. The filtrate was extracted with diethyl ether. The organic layer was concentrated and combined with the above precipitate to give the crude product. Purification was carried out by column chromatography to obtain the title compound as a brown solid (2.5 g, 30%). MS (ESI, pos. ion) m/z: 552.2 (M+1).

Workup

  1. customwas purged with argon gas for 5 min
  2. customagain purged with argon gas for 5 min
  3. additionThe reaction mixture was then poured into water
  4. filtrationThe resulting precipitate was collected by filtration
  5. extractionThe filtrate was extracted with diethyl ether
  6. concentrationThe organic layer was concentrated
  7. customto give the crude product
  8. customPurification

Sources & evidence

ORD record
ord-2ca011affbb4469c8c25b8ac75d89e83
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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