Water → HCID 66778839, compound

HRID 85061Notes

Reaction equation

HRID 85061 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:20]=[CH:19][C:14]([C:15]([NH:17][CH3:18])=[O:16])=[CH:13][CH:12]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.[CH3:31][O:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[C:37]([O:41][CH3:42])[C:38]=1[O:39][CH3:40].C([O-])([O-])=O.[Na+].[Na+].O>CC#N.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:18][NH:17][C:15](=[O:16])[C:14]1[CH:19]=[CH:20][C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:35]4[CH:36]=[C:37]([O:41][CH3:42])[C:38]([O:39][CH3:40])=[C:33]([O:32][CH3:31])[CH:34]=4)[CH:3]=3)[NH:8][CH:9]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 667789334-[5-bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-N-methyl-benzamide

Product 1

HCID 66778839HCID 66778839, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

4-[5-Bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-N-methyl-benzamide (Intermediate CE, 100 mg, 0.206 mmol), 3,4,5-trimethoxyphenylboronic acid (53 mg, 0.248 mmol) and dichlorobis(triphenylphosphine)palladium (II) (9 mg, 0.012 mmol) were combined in CH3CN (2 ml) and 1 M Na2CO3 (2 ml) and reacted in a microwave reactor for 20 min at 150° C. Water was added, the aqueous phase was extracted with DCM and the organic phase was dried and evaporated. Purification by silica gel chromatography using 0-8% MeOH:DCM yielded 40 mg (47%) of the title compound. 1H NMR (CDCl3, 300 MHz): δ 12.09 (s, 1H), 8.59 (d, J=1.2 Hz, 1H), 8.48 (d, J=1.2 Hz, 1H), 8.43 (q, J=2.7 Hz, 1H), 8.04 (s, 1H), 7.94 (d, J=4.0, 2H), 7.91 (d, J=4.0 Hz, 2H), 7.00 (s, 2H), 3.89 (s, 6H), 3.70 (s, 3H), 2.80, (d, J=4.5 Hz, 3H).

Workup

  1. extractionthe aqueous phase was extracted with DCM
  2. customthe organic phase was dried
  3. customevaporated
  4. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-f5b5654fed6548be888a062be37cb652
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Reaction notes

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