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Cesium carbonate → (1R,2S)-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)-1-phenylpentan-2-amine

HRID 13102
Notes
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Reaction equation

HRID 13102 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:12][CH2:13][CH3:14])[C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[Ar].[F:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:31]3[C:26](=[CH:27][C:28](I)=[CH:29][CH:30]=3)[CH:25]=[N:24]2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)CCC.[Cu]I>[F:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[C:31]3[C:26](=[CH:27][C:28]([O:5][C@H:4]([C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=4)[C@@H:3]([NH2:2])[CH2:12][CH2:13][CH3:14])=[CH:29][CH:30]=3)[CH:25]=[N:24]2)=[CH:21][CH:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 592511281-(4-fluorophenyl)-5-iodo-1H-indazoleHCID 86623008argon (1R,2S)-2-amino-1-phenylpentan-1-ol hydrochloride

Product 1

HCID 59339774(1R,2S)-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)-1-phenylpentan-2-amine

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 8008ButyronitrileSolvent

Conditions

Temperature
125 °C

Procedure

In a vial under argon (1R,2S)-2-amino-1-phenylpentan-1-ol hydrochloride (91b, 46 mg, 0.21 mmol), 1-(4-fluorophenyl)-5-iodo-1H-indazole (87 mg, 0.26 mmol), copper(I)iodide (8.12 mg, 0.04 mmol) and cesium carbonate (278 mg, 0.85 mmol) were mixed in butyronitrile (0.6 mL). The vial was sealed and heated to 125° C. for 16 h. The mixture was filtered through celite. The celite was washed with ethyl acetate. The collected organic phases were evaporated and the crude product was purified by preparative HPLC. The pure fractions were collected, ethyl acetate and a saturated sodium carbonate were added and the mixture was shaken. The organic layer was separated and the water layer was washed twice with ethyl acetate. The combined organic layers were dried over sodium sulphate and finally evaporated to give the pure product.

Workup

  1. customThe vial was sealed
  2. filtrationThe mixture was filtered through celite
  3. washThe celite was washed with ethyl acetate
  4. customThe collected organic phases were evaporated
  5. customthe crude product was purified by preparative HPLC
  6. customThe pure fractions were collected
  7. additionethyl acetate and a saturated sodium carbonate were added
  8. customThe organic layer was separated
  9. washthe water layer was washed twice with ethyl acetate
  10. dry with materialThe combined organic layers were dried over sodium sulphate
  11. customfinally evaporated
  12. customto give the pure product

Sources & evidence

ORD record
ord-de25f8a7ec5b4322bcb8649f1d574484
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728030B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes