Sodium Carbonate → HCID 67494482, compound

HRID 2047140Notes

Reaction equation

HRID 2047140 reaction equation
[CH3:1][Si:2]([CH3:43])([CH3:42])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[C:8]1[N:13]2[N:14]=[CH:15][C:16](I)=[C:12]2[N:11]=[C:10]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[CH2:20][CH2:19]2)[CH:9]=1.[C:44]1([C:50]2[CH:55]=[CH:54][C:53](B3OC(C)(C)C(C)(C)O3)=[CH:52][N:51]=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C([O-])([O-])=O.[Na+].[Na+]>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.COCCOC>[CH3:1][Si:2]([CH3:43])([CH3:42])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:53]3[CH:52]=[N:51][C:50]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[CH:55][CH:54]=3)=[C:12]2[N:11]=[C:10]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[CH2:20][CH2:19]2)[CH:9]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 457865262-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 67494530HCID 67494530, compound

Product 1

HCID 67494482HCID 67494482, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a pressure tube were charged benzyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate (1 g, 2.85 mmol), 2-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1.2 g, 4.1 mmol), Pd(PPh3)4 (164 mg, 0.14 mmol), DME (20 mL) and 2 M Na2CO3 (10 mL). The mixture was briefly degassed with Argon and the tube was capped and heated at 80° C. for 15 hours. On cooling, H2O (40 mL) and EtOAc (100 mL) and aqueous layer was extracted with EtOAc (3×) and combined organic layers were washed with brine once and dried (MgSO4). After concentration in vacuo the residue was purified on silica gel. Elution with EtOAc/Hexanes (0-30%) gave the title compound (1.33 g, 61%).

Workup

  1. customThe mixture was briefly degassed with Argon
  2. customthe tube was capped
  3. temperatureOn cooling
  4. extractionH2O (40 mL) and EtOAc (100 mL) and aqueous layer was extracted with EtOAc (3×)
  5. washwere washed with brine once
  6. dry with materialdried (MgSO4)
  7. concentrationAfter concentration in vacuo the residue
  8. customwas purified on silica gel
  9. washElution with EtOAc/Hexanes (0-30%)

Sources & evidence

ORD record
ord-2804fc286ba84b3290b6d4cb61b93073
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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