Hydrochloric Acid → HCID 22479712, compound

HRID 1349916Notes

Reaction equation

HRID 1349916 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[N:4](C2CCCCO2)[N:3]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH:27]=[C:26](B(O)O)[CH:25]=[CH:24]2.ClCCl.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>COCCOC.CO>[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH:27]=[C:26]([C:2]1[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=3)[NH:4][N:3]=1)[CH:25]=[CH:24]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 46416926-Methoxy-2-naphthaleneboronic acidHCID 224799453-Bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carbonitrile

Product 1

HCID 22479712HCID 22479712, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
45 °C

Procedure

The title compound was prepared as described in Example 161, using 3-bromo-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (0.500 g, 1.6 mmol), in ethylene glycol dimethyl ether (30 mL), 6-methoxynaphthalene-2-boronic acid (0.395 g, 2.0 mmol), [1,1′-bis(diphenyl phosphino-ferrocene] complex with dichloromethane (1:1) (0.133 g, 0.16 mmol) and potassium phosphate (3.5 g, 16.3 mmol). Solvent was removed using a rotary evaporator and purification of the residue by column chromatography (silica gel, 20% ethyl acetate/hexanes) gave a solid. Methanol (50 mL) and aqueous 6 N hydrochloric acid (50 mL) were added to the solid and the mixture was heated at 45° C. for 5 h. One half of the methanol was evaporated, water was added and the solid filtered and dried in a vacuum oven to afford the title compound (0.230 g, 47% yield over 2 steps): ES-MS (m/z) 300 [M+1]+.

Workup

  1. customThe title compound was prepared
  2. customSolvent was removed
  3. customa rotary evaporator and purification of the residue by column chromatography (silica gel, 20% ethyl acetate/hexanes)
  4. customgave a solid
  5. customOne half of the methanol was evaporated
  6. additionwater was added
  7. filtrationthe solid filtered
  8. customdried in a vacuum oven

Sources & evidence

ORD record
ord-5c82ea806e0a4dc391978c31fe5f56c6
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

Loading…