Potassium Phosphate, Tribasic → HCID 118021738, compound

HRID 575678Notes

Reaction equation

Br[C:2]1[CH:6]=[C:5]([S:7]([CH2:10][CH3:11])(=[O:9])=[O:8])[S:4][C:3]=1[O:12][CH2:13][CH3:14].[CH3:15][N:16]1[CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=[O:35].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:13]([O:12][C:3]1[S:4][C:5]([S:7]([CH2:10][CH3:11])(=[O:9])=[O:8])=[CH:6][C:2]=1[C:24]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:35])[N:16]([CH3:15])[CH:25]=1)[CH3:14]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3-bromo-2-ethoxy-5-ethylsulfonylthiophene (18.0 mg, 0.06 mmol), 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one (24 mg, 0.08 mmol), K3PO4 (42 mg, 0.20 mmol) and Pd(dppf)Cl2 (6 mg, 0.008 mmol) in dioxane (0.5 mL) and H2O (0.05 mL) was stirred at 60° C. for 1.5 h. The reaction mixture was then poured over water (6 mL) and extracted with EtOAc (2×5 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by normal phase silica gel column chromatography to give the title compound (10.5 mg, 46%). 1H NMR (DMSO-d6, 400 MHz) δ 8.29 (d, J=7.9 Hz, 1H), 7.71 (dd, J=7.6, 7.6 Hz, 1H), 7.57 (m, 3H), 7.35 (d, J=7.9 Hz, 1H), 4.25 (m, 2H), 3.54 (s, 3H), 3.38 (m, 2H), 1.24 (m, 6H). LCMS: 378.05 (M+1)+

Workup

extractionextracted with EtOAc (2×5 mL)
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by normal phase silica gel column chromatography

Sources & evidence

ORD record: ord-2935b999e8364e8db715acd01b9af64f
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034900B2

Reaction notes

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