1,4-Dioxane → HCID 66897145, compound

HRID 1913220Notes

Reaction equation

HRID 1913220 reaction equation
[CH3:1][Si:2]([CH3:45])([CH3:44])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20](Cl)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH2:24][CH:25]2[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH2:26]2)[CH:9]=1.[C:46]1(B(O)O)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>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.O>[CH3:1][Si:2]([CH3:45])([CH3:44])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH2:24][CH:25]2[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH2:26]2)[CH:9]=1

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 86667836HCID 86667836, compound

Product 1

HCID 66897145HCID 66897145, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

In a 2-5 mL microwave vial was charged ethyl 4-((7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-chloropyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)cyclohexanecarboxylate (Int-4k, 300 mg, 0.45 mmol), phenylboronic acid (108 mg, 0.89 mmol), K3PO4 (189 mg, 0.89 mmol), and Pd(PPh3)4 (52 mg, 0.045 mmol). To this was added 3:1 1,4-dioxane:H2O (4 mL). The vial was flushed with argon and sealed. The reaction was heated to 140° C. for 20 minutes in a microwave synthesizer. The reaction was then diluted with DCM (30 mL) and washed with H2O. The organic phase was dried over Na2SO4 and the residue was purified via silica gel chromatography to yield the title compound. Yield=265 mg.

Workup

  1. customThe vial was flushed with argon
  2. customsealed
  3. additionThe reaction was then diluted with DCM (30 mL)
  4. washwashed with H2O
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customthe residue was purified via silica gel chromatography

Sources & evidence

ORD record
ord-e5acb1440a8c4fdfa02a640179077ec1
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

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