Cesium carbonate → HCID 59786580, compound

HRID 1661481

Reaction equation

HRID 1661481 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[N:6]=[CH:5]2.[NH2:17][CH:18]([CH3:29])[CH:19]([C:21]1[CH:22]=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)[OH:20].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)CCC.C1(C)C=CC=CC=1.[Cu]I>[CH3:28][O:27][C:24]1[N:23]=[CH:22][C:21]([CH:19]([O:20][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:6]=[CH:5]3)[CH:18]([NH2:17])[CH3:29])=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 597865715-iodo-1-pyridin-3-yl-1H-indazoleHCID 59786583HCID 59786583, compound

Product 1

HCID 59786580HCID 59786580, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 8008ButyronitrileSolvent

Conditions

Temperature
130 °C

Procedure

5-Iodo-1-(3-pyridinyl)indazole (750 mg, 2.3 mmole), 2-Amino-1-[6-methoxypyridin-3-yl]propan-1-ol (410 mg, 2.2 mmol), copper(I)iodide (42 mg, 0.22 mmol) and caesium carbonate (1.45 g, 4.5 mmole) were suspended in butyronitrile (2.4 mL) and toluene (4.8 mL). The reaction vessel was capped and the mixture was stirred at 130° C. for 20 hours. Then the solvent was removed i.vac., and the product purified by chromatography on silica gel. Yield 254 mg (3 0%) as a racemic mixture of two diastereomeres.

Workup

  1. customThe reaction vessel was capped
  2. customThen the solvent was removed i.vac
  3. custom, and the product purified by chromatography on silica gel
  4. additionYield 254 mg (3 0%) as a racemic mixture of two diastereomeres

Sources & evidence

ORD record
ord-394ddf0596ae4f78ab2d49184cb624cf
Source dataset
uspto-grants-2011_10
Patent number
US08030340B2

Linked notes

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