Water → HCID 69519893, compound

HRID 855102Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH3:13])[O:8][CH:7]([C:18]([F:21])([F:20])[F:19])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5]2.[CH3:27]B1OB(C)OB(C)O1.C([O-])([O-])=O.[Cs+].[Cs+].O>COCCOCCOC>[CH2:14]([N:12]([CH3:13])[C:11]1[CH:10]=[C:9]2[C:4]([CH:5]=[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:7]([C:18]([F:21])([F:20])[F:19])[O:8]2)=[CH:3][C:2]=1[CH3:27])[CH:15]([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of ethyl 6-chloro-7-[isobutyl(methyl)amino]-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 8c (0.50 g, 1.28 mmole), trimethylboroxine (0.38 g, 2.75 mmole), [(tBu3P)PdBr]2 (0.01 g), and Cs2CO3 (0.75 g, 2.31 mmole) in anhydrous diglyme (10.0 mL) was heated to 115° C. under a dry N2 atmosphere for 18 hrs. The contents were poured into water (40 ml) and extracted with EtOAc (2×40 mL). The combined extracts were washed with brine (20 mL), dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil which was subject to HPLC (reverse phase) and eluted with 50-85% ACN/water with 0.05% TFA to give yellow solid (0.21 g, 45%). No further purification was performed. GCMS m/z 371.0 (M+). LCMS m/z 372.0 (M+H).

Workup

extractionextracted with EtOAc (2×40 mL)
washThe combined extracts were washed with brine (20 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a yellow oil which
washeluted with 50-85% ACN/water with 0.05% TFA

Sources & evidence

ORD record: ord-a203eb6dbe244002a562ef86316e7429
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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