Hydrochloric Acid → HCID 22479906, compound

HRID 1349905Notes

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[CH2:23][CH2:22][C:21]2[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][C:20]1=2.ClCCl.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>COCCOC.O.CO>[O:19]1[CH2:23][CH2:22][C:21]2[CH:24]=[C:25]([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:26]=[CH:27][C:20]1=2

Participants

Conditions

Temperature: 45 °C

Procedure

The title compound was prepared as described in Example 411, using 3-bromo-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (0.750 g, 2.45 mmol), in ethylene glycol dimethyl ether (50 mL), 2,3-dihydrobenzo[b]furan-5-boronic acid (0.480 g, 2.9 mmol), [1,1′-bis(diphenylphosphino-ferrocene] complex with dichloromethane (1:1) (0.200 g, 0.20 mmol) and potassium phosphate (5.2 g, 24 mmol). Solvent was removed using a rotary evaporator and purification of the residue by column chromatography (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. Water (40 mL) was added and the solid was filtered and dried in a vacuum oven to afford the title compound (0.350 g, 64% yield over 2 steps): ES-MS (m/z) 262 [M+1]+.

Workup

customThe title compound was prepared
customSolvent was removed
customa rotary evaporator and purification of the residue by column chromatography (20% ethyl acetate/hexanes)
customgave a solid
filtrationthe solid was filtered
customdried in a vacuum oven

Sources & evidence

ORD record: ord-ea0a5520db724e20a60b2f8157e5f3d3
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211594B2

Reaction notes

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