Potassium Carbonate → HCID 178515524, compound

HRID 1784809Notes

Reaction equation

HRID 1784809 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH:17]=[CH:18][N:19]3[Si](C(C)C)(C(C)C)C(C)C)[N:12]=[C:11]([NH:34][C:35]2[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=2)[N:10]=1)C1C=CC=CC=1.C(OC1C=C(Cl)N=C(NC2C=NC=CC=2)N=1)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].CC1(C)C(C)(C)OB(C2C=CC=C3C=2C=CN3[Si](C(C)C)(C(C)C)C(C)C)O1>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.O1CCOCC1.CN(C=O)C>[NH:19]1[C:20]2[C:16](=[C:15]([C:13]3[N:12]=[C:11]([NH:34][C:35]4[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=4)[N:10]=[C:9]([OH:8])[CH:14]=3)[CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:18]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 27955744-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-(triisopropylsilyl)-1H-indoleHCID 68841675[4-Benzyloxy-6-(1-triisopropylsilanyl-1h-indol-4-yl)-pyrimidin-2-yl]-pyridin-3-yl-amineHCID 87596721(4-Benzyloxy-6-chloro-pyrimidin-2-yl)-pyridin-3-yl-amine

Product 1

HCID 178515524HCID 178515524, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

[4-Benzyloxy-6-(1-triisopropylsilanyl-1H-indol-4-yl)-pyrimidin-2-yl]-pyridin-3-yl-amine. DMF (1 mL) and dioxane (2 mL) were added through a septum to a nitrogen-purged microwave tube containing (4-benzyloxy-6-chloro-pyrimidin-2-yl)-pyridin-3-yl-amine (80 mg, 0.256 mmol), potassium carbonate (71 mg, 0.50 mmol), Pd(PPh3)4 (59 mg, 0.51 mmol), and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole (153 mg, 0.384 mmol). The mixture was subjected to microwave conditions 100 W/130° C. for 1 hour. SFC/MS analysis showed mostly the desired product. A small amount of product with loss of the TIPS group was seen as well. The reaction mixture was cooled to room temperature and filtered through Celite®. The solvent was concentrated and the crude mixture was purified by a short silica column with 99:1 methylene chloride/MeOH solvent mixture to afford 100 mg of [4-benzyloxy-6-(1-triisopropylsilanyl-1H-indol-4-yl)-pyrimidin-2-yl]-pyridin-3-yl-amine (˜75% pure by SFC/MS). This material was used without further purification.

Workup

  1. custompurged microwave tube
  2. customconditions 100 W/130° C.
  3. customfor 1 hour

Sources & evidence

ORD record
ord-8c2653f0cac1492cbf088944d2dd581a
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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