Potassium Carbonate → HCID 25123579, compound

HRID 1693733Notes

Reaction equation

HRID 1693733 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[CH:6][N:5]=[C:4]2[NH:19][CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])[C:3]=12.[CH3:30]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+]>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.O1CCOCC1>[CH3:29][O:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:21]1[C:3]2[C:4](=[N:5][CH:6]=[C:7]([C:8]3[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=3)[C:11]([N:13]([CH3:14])[CH3:15])=[O:12])[C:2]=2[CH3:30])[NH:19][CH:20]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 25123577HCID 25123577, compound

Product 1

HCID 25123579HCID 25123579, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Into a 5 mL Personal Chemistry microwave reaction vial were added 3-[4-Chloro-3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide (37 mg, 0.09 mmol), trimethylboroxine (15 μL, 0.11 mmol), tetrakis(triphenylphosphine)palladium (7 mg, 0.009 mmol), potassium carbonate (52 mg, 0.27 mmol), and dioxane (1 mL). The vial was purged with nitrogen, sealed, and irradiated in a Personal Chemistry Optimizer at 140° C. for 60 min. The reaction mixture was diluted with ethylacetate, filtered over Celite and concentrated. The crude product was purified by mass triggered reverse phase HPLC to afford the title compound (2.4 mg, 0.006 mmol, 7% yield). 1H NMR (500 MHz, DMSO-d6) δ 11.74 (d, J=2 Hz, 1H), 8.32 (s, 1H), 8.04 (s, 1H), 7.50 (t, J=8 Hz, 1H), 7.41 (dt, J1=9.5 Hz, J2=1.5 Hz, 1H), 7.37 (dt, J=7.5 Hz, J2=1.5 Hz, 1H), 7.33 (m, 4H), 7.26 (dd, J1=7 Hz, J2=2 Hz, 1H), 7.04 (d, J=7.5 Hz, 1H), 6.97 (td, J=7.5 Hz, J2=1 Hz, 1H), 3.70 (s, 3H), 2.97 (bs, 3H), 2.93 (bs, 3H), 2.04 (s, 3H). MS: m/z 386.2 (M+H+).

Workup

  1. customInto a 5 mL Personal Chemistry microwave reaction
  2. customThe vial was purged with nitrogen
  3. customsealed
  4. customirradiated in a Personal Chemistry Optimizer at 140° C. for 60 min
  5. additionThe reaction mixture was diluted with ethylacetate
  6. filtrationfiltered over Celite
  7. concentrationconcentrated
  8. customThe crude product was purified by mass triggered reverse phase HPLC

Sources & evidence

ORD record
ord-981859395185476caeec170b1e99a074
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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