Water → HCID 67531314, compound

HRID 2388226Notes

Reaction equation

[OH:1][C:2]1[C:3]2[O:16][N:15]=[C:14]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[C:4]=2[C:5](I)=[N:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH:22]1(B(O)O)[CH2:24][CH2:23]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH:22]1([C:5]2[C:4]3[C:14]([C:17]4[S:18][CH:19]=[CH:20][CH:21]=4)=[N:15][O:16][C:3]=3[C:2]([OH:1])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=2)[CH2:24][CH2:23]1

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 7-hydroxy-4-iodo-3-(thiophen-2-yl)isoxazolo[4,5-c]pyridine-6-carboxylate (300 mg, 0.72 mmol), cyclopropylboronic acid (74 mg, 0.87 mmol), K3PO4 (505 mg, 2.38 mmol) and Pd(PPh3)4 (83 mg, 0.072 mmol) were added to a flask, and the flask evacuated. After refilling with nitrogen, toluene (4 mL) and water (43 μl, 2.38 mmol) were added, and the resulting suspension was heated in an oil bath (T=100° C.) for 18 h. After the mixture was cooled to room temperature, the mixture was diluted with EtOAc (50 mL) and the solid was removed by filtration. The filtrate was concentrated and the residue was purified first by flash chromatography (0-40% EtOAc/hexanes), then by preparative TLC (eluted with 40% EtOAc/hexanes), to afford 47 mg of the title compound. MS: (+) m/z 331.24 (M+1).

Workup

customthe flask evacuated
additionwere added
temperatureAfter the mixture was cooled to room temperature
customthe solid was removed by filtration
concentrationThe filtrate was concentrated
customthe residue was purified first by flash chromatography (0-40% EtOAc/hexanes)
washby preparative TLC (eluted with 40% EtOAc/hexanes)

Sources & evidence

ORD record: ord-4d68ea487c1a4999bf1f26728599beb6
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08269008B2

Reaction notes

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