Sodium Carbonate → HCID 67319277, compound

HRID 1711597Notes

Reaction equation

HRID 1711597 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[CH2:17][C@H:16]3[NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])=[CH:11][CH:10]=2)O1.C([O-])([O-])=O.[Na+].[Na+].O1[CH2:37][CH2:36]OCC1>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>[CH3:17][C:16]1[N:18]=[CH:37][C:36]([C:9]2[CH:10]=[CH:11][C:12]([C@@H:15]3[CH2:17][C@H:16]3[NH:18][S:19]([CH:22]([CH3:23])[CH3:24])(=[O:20])=[O:21])=[CH:13][CH:14]=2)=[CH:12][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 67319244HCID 67319244, compound2×

Product 1

HCID 67319277HCID 67319277, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst2×

Conditions

Temperature
90 °C

Procedure

In an 8 ml vial (PLS apparatus) the bromoaryl reagent (3-bromo-6-methylpyridine for Example 2) (0.328 mmol) was placed together with a solution of trans-N-{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropyl}-2-propanesulfonamide (Intermediate 8) (60 mg, 0.164 mmol) in dry 1,4-dioxane (1.0 ml). Polymer supported Tetrakis catalyst (Pol-Pd(PPh3)4) (15 mg, 0.00164 mmol), and Na2CO3 2M (0.205 ml, 0.41 mmol) were added. The reaction mixture was shaken at 90° C. for 3-4 h (if reaction not complete by LC/MS analysis then heated for an additional 3 h) then left at room temperature overnight. The resin was filtered off (by Alltech filter tube) and washed with dichloromethane, water, methanol and dichloromethane. The liquid phase was evaporated until dryness under reduced pressure and the residue was taken up in dichloromethane (2 ml) and washed with HCl 1M (1 ml) then the acidic solution was basified with K2CO3 2M and extracted with dichloromethane (2×1 ml). The combined organic extracts were concentrated under reduced pressure to give a crude oil which was purified by reverse phase HPLC to give the title compound. The HPLC conditions were as given in “Preparative Chromatography” above.

Workup

  1. additionwere added
  2. customif reaction not complete by LC/MS analysis
  3. temperaturethen heated for an additional 3 h)
  4. waitthen left at room temperature overnight
  5. filtrationThe resin was filtered off
  6. filtration(by Alltech filter tube)
  7. washwashed with dichloromethane, water, methanol and dichloromethane
  8. customThe liquid phase was evaporated until dryness under reduced pressure
  9. washwashed with HCl 1M (1 ml)
  10. extractionextracted with dichloromethane (2×1 ml)
  11. concentrationThe combined organic extracts were concentrated under reduced pressure
  12. customto give a crude oil which
  13. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-ec5df7b8aeda4f6f89d48a516d3364d9
Source dataset
uspto-grants-2010_09
Patent number
US07790758B2

Reaction notes

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