Sodium Carbonate → HCID 46236050, compound

HRID 85070Notes

Reaction equation

HRID 85070 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][CH:19]=3)[NH:16][CH:15]=[CH:14]4)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:38]2[CH:57]=[CH:56][C:41]([CH2:42][N:43]3[CH2:48][CH2:47][N:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:45][CH2:44]3)=[CH:40][CH:39]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[NH:16]1[C:17]2[C:18](=[CH:19][C:11]([C:10]3[C:4]4[C:5](=[N:6][CH:7]=[C:2]([C:38]5[CH:57]=[CH:56][C:41]([CH2:42][N:43]6[CH2:44][CH2:45][N:46]([C:49]([O:51][C:52]([CH3:53])([CH3:55])[CH3:54])=[O:50])[CH2:47][CH2:48]6)=[CH:40][CH:39]=5)[CH:3]=4)[NH:8][CH:9]=3)=[CH:12][CH:13]=2)[CH:14]=[CH:15]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 53216820tert-Butyl 4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl)piperazine-1-carboxylateHCID 667791765-bromo-3-(1H-indol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 46236050HCID 46236050, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

Intermediate B (131 mg) and tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperazine-1-carboxylate (136 mg) were suspended in 2 mL of acetonitrile and treated with 2 mL of 1 M sodium carbonate solution and dichloro-bis-(triphenylphosphine)-palladium(II) (10 mg). The resulting mixture was heated in a microwave reactor cell for 20 minutes at 150° C., resulting in de-tosylated material which was purified by MPLC chromatography (0-3% methanol) to provide an analytical sample of the title compound (50 mg, 508 M+H).

Workup

  1. customresulting in de-tosylated material which
  2. customwas purified by MPLC chromatography (0-3% methanol)

Sources & evidence

ORD record
ord-24db11e5b65d41f59a52f56ecaa2e73a
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Reaction notes

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