Sodium Carbonate → HCID 57819874, compound

HRID 657300Notes

Reaction equation

HRID 657300 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:9][NH:10][C:11](=[O:37])[CH2:12][C:13]([NH:15][CH2:16][C:17]2[C:18]([NH:30][CH:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[C:19]3[CH:27]=[N:26][N:25]([CH2:28][CH3:29])[C:20]3=[N:21][C:22]=2[CH2:23][CH3:24])=[O:14])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH:38]([C:40]1[CH:41]=[C:42](B(O)O)[CH:43]=[CH:44][CH:45]=1)=[O:39].C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>CCOC(C)=O.O.[Pd].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.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>[CH2:28]([N:25]1[C:20]2=[N:21][C:22]([CH2:23][CH3:24])=[C:17]([CH2:16][NH:15][C:13](=[O:14])[CH2:12][C:11]([NH:10][CH2:9][C:4]3[CH:3]=[C:2]([C:44]4[CH:43]=[CH:42][CH:41]=[C:40]([CH:38]=[O:39])[CH:45]=4)[C:7]([CH3:8])=[CH:6][CH:5]=3)=[O:37])[C:18]([NH:30][CH:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[C:19]2[CH:27]=[N:26]1)[CH3:29]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27343563-Formylphenylboronic acidHCID 57819883HCID 57819883, compound

Product 1

HCID 57819874HCID 57819874, compoundYield 32.8%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[(3-bromo-4-methylphenyl)methyl]-N′-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}propanediamide (1.3 g, 2.275 mmol), (3-formylphenyl)boronic acid (0.428 g, 2.85 mmol), tetrakis (triphenylphosphine) palladium (0) (0.093 g, 0.080 mmol), sodium carbonate (0.610 g, 5.76 mmol), and 1,4-dioxane (14 mL) and water (5 mL), while stirring under N2, was microwaved at 140° C. for 30 min. The reaction mixture was diluted with EtOAc and water. The organic layer was recovered and washed with saturated NaCl, dried over Na2SO4, and then evaporated to viscous taffy. The viscous taffy was purified on a Chromatotron Plate Silica Gel (1000μ) eluting with CH2Cl2— MeOH (97:3) to afford N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N′-[(3′-formyl-6-methyl-3-biphenylyl)methyl]propanediamide (69.7 mg, 32.8%) as a viscous, nearly colorless, foam, taffy. LC-MS m/z 597.5 (M+H)+, 0.87 min (ret time).

Workup

  1. customwas microwaved at 140° C. for 30 min
  2. customThe organic layer was recovered
  3. washwashed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated to viscous taffy
  6. customThe viscous taffy was purified on a Chromatotron Plate Silica Gel (1000μ)
  7. washeluting with CH2Cl2— MeOH (97:3)

Sources & evidence

ORD record
ord-083d5d35641245378abbdcb8cce08ea3
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Reaction notes

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