tert-Butyl 3-iodo-5-nitro-1H-indole-1-carboxylate → HCID 67959775, compound

HRID 1529355Notes

Reaction equation

HRID 1529355 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[CH:14][CH:15]=2)[C:10](I)=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:26]1[N:31]=[C:30]([N:32]2[CH2:37][CH2:36][CH:35]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:34][CH2:33]2)[CH:29]=[N:28][CH:27]=1)CCC>CN(C=O)C.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]([O:40][C:39]([NH:38][CH:35]1[CH2:36][CH2:37][N:32]([C:30]2[N:31]=[C:26]([C:10]3[C:11]4[C:16](=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=4)[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:9]=3)[CH:27]=[N:28][CH:29]=2)[CH2:33][CH2:34]1)=[O:45])([CH3:44])([CH3:42])[CH3:43]

Participants

5

Reactant 2

HCID 40428559tert-Butyl 3-iodo-5-nitro-1H-indole-1-carboxylateHCID 86709776HCID 86709776, compound

Product 1

HCID 67959775HCID 67959775, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-Iodo-5-nitro-indole-1-carboxylic acid tert-butyl ester (480 mg, 1.23 mmol) and tert-butyl 1-(6-(tributylstannyl)pyrazin-2-yl)piperidin-4-ylcarbamate 1d (700 mg, 1.23 mmol) in DMF (4.8 mL) was purged with argon gas for 5 min and added Cut (352 mg, 1.84 mmol) and palladium tetrakis (171 mg, 0.15 mmol). The resulting mixture was purged with argon gas for 5 min and stiffed under nitrogen atmosphere at 90° C. 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 white solid (200 mg, 30%). MS (ESI, pos. ion) m/z: 539.3 (M+1).

Workup

  1. customwas purged with argon gas for 5 min
  2. customThe resulting mixture was 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-f556da950a244f36a015c6e3baa701cb
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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