Hydrochloric Acid → HCID 22480165, compound

HRID 1353971Notes

Reaction equation

HRID 1353971 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.[O:19]1[C:24]2[CH:25]=[CH:26][C:27](B(O)O)=[CH:28][C:23]=2[O:22][CH2:21][CH2:20]1.ClCCl.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>COCCOC.O.CO>[O:19]1[C:24]2[CH:25]=[CH:26][C:27]([C:2]3[C:10]4[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=4)[NH:4][N:3]=3)=[CH:28][C:23]=2[O:22][CH2:21][CH2:20]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 2776178(2,3-Dihydro-1,4-benzodioxin-6-yl)boronic acidHCID 224799453-Bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carbonitrile

Product 1

HCID 22480165HCID 22480165, compoundYield 72.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
45 °C

Procedure

The title compound was prepared using 3-bromo-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (0.354 g, 1.15 mmol), in ethylene glycol dimethyl ether (20 mL), 2H,3H-benzo[e]1,4-dioxin-6-boronic acid (0.250 g, 1.39 mmol), [1,1′-bis(diphenyl phosphino-ferrocene] complex with dichloromethane (1:1) (0.094 g, 0.11 mmol) and potassium phosphate (2.40 g, 11.5 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 (30 mL) and aqueous 6 N hydrochloric acid (30 mL) were added to the solid and the mixture was heated at 45° C. for 5 h. Water (30 mL) was added and the solid was filtered and dried in a vacuum oven to afford the title compound (0.230 g, 71% yield over 2 steps): ES-MS (m/z) 278 [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. filtrationthe solid was filtered
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-d4e877ba84c04cbb8d44cbd9047d6566
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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