Sodium Carbonate → HCID 25123580, compound

HRID 1693720Notes

Reaction equation

HRID 1693720 reaction equation
[Cl:1][C:2]1[C:7](B2OC(C)(C)C(C)(C)O2)=[CH:6][N:5]=[C:4]2[N:17](COCC[Si](C)(C)C)[CH:18]=[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH3:27])[C:3]=12.Br[C:37]1[CH:38]=[C:39]([CH:43]([OH:49])[C:44]([N:46]([CH3:48])[CH3:47])=[O:45])[CH:40]=[N:41][CH:42]=1.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[Cl:1][C:2]1[C:7]([C:37]2[CH:38]=[C:39]([CH:43]([OH:49])[C:44]([N:46]([CH3:47])[CH3:48])=[O:45])[CH:40]=[N:41][CH:42]=2)=[CH:6][N:5]=[C:4]2[NH:17][CH:18]=[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH3:27])[C:3]=12

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 57537496HCID 57537496, compoundHCID 57537619HCID 57537619, compound

Product 1

HCID 25123580HCID 25123580, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

Into a 5 mL Personal Chemistry microwave reaction vial were added 4-Chloro-3-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (38 mg, 0.075 mmol), 2-(5-Bromo-pyridin-3-yl)-2-hydroxy-N,N-dimethyl-acetamide (29 mg, 0.12 mmol; preparation described below), 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichloromethane adduct (3 mg, 0.004 mmol), acetonitrile (1 mL) and saturated aqueous Na2CO3 (75 μL). The vial was purged with nitrogen, sealed, and irradiated in a Personal Chemistry Optimizer at 120° C. for 30 min. Sodium sulfate was added to the reaction mixture and the slurry was filtered over Celite and concentrated. The crude product was dissolved in 1 mL TFA and stirred at 23° C. for 15 min. The solvent was evaporated and the resulting oil was dissolved in 1 mL DMSO and 50 μL ethylenediamine and purified by mass triggered reverse phase HPLC to afford the title compound (9.5 mg, 0.015 mmol, 25% yield). 1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.58 (m, 2H), 8.20 (s, 1H), 7.83 (t, J=2 Hz, 1H), 7.33 (td, J=8 Hz, J2=1.5 Hz, 1H), 7.27 (dd, J=7 Hz, J2=1.5 Hz, 1H), 7.05 (d, J=8 Hz, 1H), 6.95 (td, J=8 Hz, J2=1 Hz, 1H), 5.81 (d, J=6.5 Hz, 1H), 5.56 (d, J=6.5 Hz, 1H), 3.68 (s, 3H), 2.95 (s, 3H), 2.84 (s, 3H). MS: m/z 437.0 (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 120° C. for 30 min
  5. additionSodium sulfate was added to the reaction mixture
  6. filtrationthe slurry was filtered over Celite
  7. concentrationconcentrated
  8. dissolutionThe crude product was dissolved in 1 mL TFA
  9. customThe solvent was evaporated
  10. dissolutionthe resulting oil was dissolved in 1 mL DMSO
  11. custom50 μL ethylenediamine and purified by mass triggered reverse phase HPLC

Sources & evidence

ORD record
ord-91354a01996f4175adcce3c90ab91b78
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

Loading…