Dichloromethane → 3-(1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}phenylamine

HRID 1353758Notes

Reaction equation

HRID 1353758 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:15]=[CH:14][N:13]([C:16]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:12]=3)[CH:9]=2)[N:4]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[N:3]=1.ClCCl.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.NC1C=C(B(O)O)C=CC=1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[O:36]1[CH2:37][CH2:38][CH2:39][CH2:40][CH:35]1[N:4]1[C:5]2[C:10](=[CH:9][C:8]([C:11]3[N:15]=[CH:14][N:13]([C:16]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:12]=3)=[CH:7][CH:6]=2)[C:2]([C:7]2[CH:6]=[C:5]([NH2:4])[CH:10]=[CH:9][CH:8]=2)=[N:3]1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 22479811HCID 22479811, compound

Product 1

HCID 211011823-(1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}phenylamineYield 79%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 80711,2-DimethoxyethaneSolventHCID 922693-Aminophenylboronic acidSolvent

Procedure

To a solution of 2-{3-bromo-5-[1 (triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazolyl}perhydro-2H-pyran (1.0 g, 1.69 mmol) in ethylene glycol dimethyl ether, (20 mL), 3-amino phenyl boronic acid was added as a solid (0.393 g, 2.53 mmol), followed by [1,1′-bis(diphenylphosphino)-ferrocene] complex with dichloromethane (1:1) (0.196 g, 0.169 mmol), and potassium phosphate (1.79 g, 8.45 mmol). The reaction mixture was heated to reflux temperature of the solvent for 12 h. The crude reaction mixture was partitioned between ethyl acetate and water. The organic extracts were dried over Na2SO4. The desired product was isolated as a beige solid after column chromatography purification (SiO2, 25–50% ethyl acetate in hexanes) (0.801 g, 79% yield): ES-MS (m/z) 603 [M+1]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature of the solvent for 12 h
  3. customThe crude reaction mixture
  4. customwas partitioned between ethyl acetate and water
  5. dry with materialThe organic extracts were dried over Na2SO4

Sources & evidence

ORD record
ord-fb4d3cd56a8540efac47b209ec968768
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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