Acetonitrile → HCID 59699932, compound

HRID 901511Notes

Reaction equation

HRID 901511 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:17]([C:18]4[CH:23]=[CH:22][C:21]([O:24]S(C5C=CC(C)=CC=5)(=O)=O)=[CH:20][CH:19]=4)=[CH:16][N:15](S(C4C=CC(C)=CC=4)(=O)=O)[C:12]3=[N:13][CH:14]=2)O1.C(#N)C.C(=O)([O-])[O-].[Na+].[Na+].Br[C:56]1[N:57]([CH3:61])[CH:58]=[CH:59][N:60]=1>CS(C)=O.CO>[CH3:61][N:57]1[CH:58]=[CH:59][N:60]=[C:56]1[C:9]1[CH:10]=[C:11]2[C:17]([C:18]3[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=3)=[CH:16][NH:15][C:12]2=[N:13][CH:14]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 27732622-Bromo-1-methyl-1H-imidazoleHCID 59699923HCID 59699923, compound

Product 1

HCID 59699932HCID 59699932, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

50 mg (80 μmol) of toluene-4-sulfonic acid 4-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-yl]-phenyl ester and 7 mg of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)-dichloride dichloromethane adduct were placed in a Smith® vial. 1 ml of acetonitrile, 1 ml of a 2 M aqueous solution of sodium carbonate and 16 μl of 2-bromo-1-methyl-1H-imidazole were added and the resulting mixture was irradiated in a Personal Chemistry microwave reactor to 165° C. for 20 min. The resulting mixture was diluted with 2 ml of DMSO and 1 ml of methanol and subsequently filtered over sodium sulfate and a 0.45 μm PTFE syringe filter. The filtrate is directly purified via mass-triggered reverse phase HPLC to afford 12 mg (41 μmol, 52% yield) of 4-[5-(1-methyl-1H-imidazol-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-yl]-phenol as a colorless solid. 1H-NMR (d6-DMSO): δ 11.97 (s, 1H), 9.40 (s, 1H), 8.53 (d, J=2.0 Hz, 1H), 8.40 (d, J=1.4 Hz, 1H), 8.14 (s, 1H), 7.77 (d, J=2.4 Hz, 1H), 7.54 (d, J=8.3 Hz, 2H), 7.30 (s, 1H), 7.02 (s, 1H), 6.86 (d, J=8.7 Hz, 2H), 3.78 (s, 3H); MS: m/z 291 [MH+].

Workup

  1. customthe resulting mixture was irradiated in a Personal Chemistry microwave reactor to 165° C. for 20 min
  2. filtrationsubsequently filtered over sodium sulfate
  3. filtrationa 0.45 μm PTFE syringe filter
  4. customThe filtrate is directly purified via mass-triggered reverse phase HPLC

Sources & evidence

ORD record
ord-da3c8074a7e7453991f66e938adde043
Source dataset
uspto-grants-2008_04
Patent number
US07361764B2

Reaction notes

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