Potassium Phosphate, Tribasic → HCID 86651973, compound

HRID 1615311Notes

Reaction equation

I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:3]=1.[CH:21]1(B(O)O)[CH2:23][CH2:22]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.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>[CH:21]1([C:2]2[C:10]3[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=3)[N:4]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:3]=2)[CH2:23][CH2:22]1

Participants

Conditions

Temperature: 97.5 °C

Procedure

A degassed mixture of 3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (51 mg, 0.12 mmol), cyclopropylboronic acid (21 mg, 0.24 mmol), powdered K3PO4 (103 mg, 0.48 mmol) and Pd(PPh3)4 (10 mg, 0.009 mmol) in PhMe (2 mL) and H2O (0.1 mL) was heated with stirring in a sealed tube under Ar at 95-100° C. for 1 d. The crude mixture was concentrated and purified by prepTLC (SiO2 5:1 hexanes/EtOAc) to provide the title compound as a clear oil (40 mg, quant): 1H NMR (400 MHz, CDCl3) δ ppm 10.13 (s, 1H), 8.02 (s, 1H), 7.87 (d, J=8.28 Hz, 1H), 7.70 (d, J=8.28 Hz, 1H), 5.71 (s, 2H), 3.54 (d, J=8.53 Hz, 2H), 2.19-2.28 (m, 1H), 1.06-1.12 (m, 4H), 0.89 (d, J=8.28 Hz, 2H), −0.07 (s, 9H); MS ESI 317.1 [M+H]+, calcd for [C17H24N2O2Si+H]+ 317.5.

Workup

temperaturewas heated
concentrationThe crude mixture was concentrated
custompurified by prepTLC (SiO2 5:1 hexanes/EtOAc)

Sources & evidence

ORD record: ord-e7ab9404520c43eea7ccadd63c46492d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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