Hydrochloric Acid → HCID 57731579, compound

HRID 2234698Notes

Reaction equation

HRID 2234698 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[C:9](S(N3C4=NC=CC=C4C=C3)(=O)=O)[N:8]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:5]2=[N:6][CH:7]=1.[NH:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][C:41]=2B(O)O)[CH:36]=[CH:35]1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+].Cl>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].C(#N)C.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:41]3[CH:40]=[CH:39][CH:38]=[C:37]4[C:42]=3[NH:34][CH:35]=[CH:36]4)=[CH:9][N:8]([S:24]([C:27]3[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=3)(=[O:26])=[O:25])[C:5]2=[N:6][CH:7]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 2763287Indole-7-boronic acidHCID 86630893HCID 86630893, compound

Product 1

HCID 57731579HCID 57731579, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 53485975CID 53485975CatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-bromo-3-iodo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (sulfonyl)-1H-pyrrolo[2,3-b]pyridine (1 g, 2.1 mmol) and 1H-indole-7-boronic acid (338 mg, 2.1 mmol) in a 20 mL microwave reaction flask was added THF (6.5 mL), acetonitrile (6.5 mL) and sodium carbonate (6.5 mL, 1 N aqueous solution, 6.5 mmol). The mixture was purged with nitrogen for 1 minute. Dichloro[1,1′-bis(diphenylphoshino)ferrocene]-palladium(II) dichloromethane adduct (164 mg, 0.2 mol) was added and the purging continued for another minute. The flask was sealed and irradiated in a microwave reactor to 60° C. for 30 minutes. Saturated sodium chloride (15 mL) was added and the pH was adjusted to 7 using hydrochloric acid (1 N). The resulting mixture was extracted with ethyl acetate (10 mL×3). The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane to afford 5-bromo-3-(1H-indol-7-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine as a light brown solid (802 mg, 82% yield). MS: m/z 466 (M+H+).

Workup

  1. customin a 20 mL microwave reaction flask
  2. customThe mixture was purged with nitrogen for 1 minute
  3. customThe flask was sealed
  4. customirradiated in a microwave reactor to 60° C. for 30 minutes
  5. extractionThe resulting mixture was extracted with ethyl acetate (10 mL×3)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane

Sources & evidence

ORD record
ord-e8439aa1bbb84493aa45f27d692018ae
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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