Water → HCID 66699199, compound

HRID 1095968Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:25])[C:9]([OH:24])([C:14]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][N:18]=[CH:19]2)[C:10]([F:13])([F:12])[F:11].[F:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][C:40]=1[C:41]([O:43][CH3:44])=[O:42].O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH3:44][O:43][C:41]([C:40]1[CH:39]=[CH:38][C:37]([C:4]2[CH:5]=[CH:6][C:7]([CH:8]([CH3:25])[C:9]([OH:24])([C:14]3[CH:23]=[CH:22][CH:21]=[C:16]4[C:15]=3[CH:20]=[CH:19][N:18]=[CH:17]4)[C:10]([F:12])([F:13])[F:11])=[C:2]([Cl:1])[CH:3]=2)=[CH:36][C:35]=1[F:34])=[O:42]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of trifluoromethanesulfonic acid 3-chloro-4-(3,3,3-trifluoro-2-hydroxy-2-isoquinolin-5-yl-1-methyl-propyl)-phenyl ester (86 mg), 3-fluoro-4-methoxycarbonylphenyl-boronic acid (50 mg) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]dichloromethane adduct (7 mg) in dioxane (0.5 ml) under argon were added water (0.4 ml) and a 2 M aqueous sodium carbonate solution (0.25 ml). The mixture was stirred at 80° C. for 5 h. The mixture was filtered and to the filtrate was added water. The mixture was extracted with EtOAc. The organic phase was dried (MgSO4), filtered and concentrated. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>2:3) to give the title compound (12 mg) as a colorless solid.

Workup

filtrationThe mixture was filtered and to the filtrate
additionwas added water
extractionThe mixture was extracted with EtOAc
dry with materialThe organic phase was dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>2:3)

Sources & evidence

ORD record: ord-e142f57c41c348e6ab4bc7bb85f541c3
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138189B2

Reaction notes

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