Sodium Carbonate → HCID 86654733, compound

HRID 2092849Notes

Reaction equation

HRID 2092849 reaction equation
I[C:2]1[C:3]2[CH2:33][NH:32][C:31](=[O:34])[C:4]=2[C:5]([NH:23][C:24]2[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].CC1(C)C(C)(C)OB([C:43]2[CH:47]=[CH:46][N:45]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[N:44]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:18]([O:17][C:16]([NH:15][C@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C@H:9]1[NH:8][C:7]1[N:6]=[C:5]([NH:23][C:24]2[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)[C:4]2[C:31](=[O:34])[NH:32][CH2:33][C:3]=2[C:2]=1[C:47]1[CH:43]=[N:44][N:45]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH:46]=1)=[O:22])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 46705337tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 86654729HCID 86654729, compound

Product 1

HCID 86654733HCID 86654733, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To an oven dried vial was added tert-butyl (1S,2R)-2-(7-iodo-3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (40 mg, 0.069 mmol), tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (30.6 mg, 0.104 mmol), and sodium carbonate (0.104 mL, 0.208 mmol) in DMF (1 mL). The resulting tan mixture was degassed 15 min. Bis(triphenylphosphine) palladium(II) chloride (4.86 mg, 6.93 μmol) was added and the mixture was degassed an additional 5 min. The vial was capped and was heated at 80° C. for 12 h. The reaction mixture was diluted with EtOAc (10 mL) and washed with water (5 mL) and brine (5 mL). The organic layer was collected, dried with Na2SO4 and concentrated to give a brown residue, which was used without further purification (55 mg). LCMS indicated the desired mass less one of the Boc protecting groups. [M+H-Boc] calc'd for C33H43N7O5, 518. found, 518.

Workup

  1. customTo an oven dried vial
  2. customThe resulting tan mixture was degassed 15 min
  3. customthe mixture was degassed an additional 5 min
  4. customThe vial was capped
  5. additionThe reaction mixture was diluted with EtOAc (10 mL)
  6. washwashed with water (5 mL) and brine (5 mL)
  7. customThe organic layer was collected
  8. dry with materialdried with Na2SO4
  9. concentrationconcentrated
  10. customto give a brown residue, which
  11. customwas used without further purification (55 mg)

Sources & evidence

ORD record
ord-0ff31c3d0ff64de2b744568158bd9b9a
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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