Sodium Bicarbonate → HCID 86598873, compound

HRID 1726080Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.C(=O)(O)[O-].[Na+].C(OC([N:21]1[C:29]2[C:24](=[CH:25][C:26]([P:30]([O:34][CH3:35])([O:32][CH3:33])=[O:31])=[CH:27][CH:28]=2)[C:23](I)=[N:22]1)=O)(C)(C)C>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.CN(C)C=O>[CH3:35][O:34][P:30]([C:26]1[CH:25]=[C:24]2[C:29](=[CH:28][CH:27]=1)[NH:21][N:22]=[C:23]2[C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:31])[O:32][CH3:33]

Participants

Conditions

Temperature: 130 °C

Procedure

44.8 mg (0.25 eq; 0.039 mmol) of tetrakis(triphenylphosphine)palladium(0), 39.6 mg (2 eq; 0.310 mmol) of 2-thiopheneboronic acid, 3 ml of dimethylformamide and 150 μl of saturated sodium bicarbonate solution are added to 70 mg (1 eq; 0.155 mol) of 5-(dimethoxyphosphoryl)-3-iodoindazole-1-carboxylic acid tert-butyl ester. The medium is stirred at 130° C. for 5 hours. The reaction medium is filtered through paper and the solvent is evaporated off under reduced pressure in a rotary evaporator. The reaction crude is purified by LC/MS to obtain 2 mg of (3-thiophen-2-yl-1H-indazol-5-yl)phosphonic acid dimethyl ester (40% purity by NMR), along with 12.9 mg of (3-thiophen-2-yl-1H-indazol-5-yl)phosphonic acid monomethyl ester.

Workup

filtrationThe reaction medium is filtered through paper
customthe solvent is evaporated off under reduced pressure in a rotary evaporator
customThe reaction crude
customis purified by LC/MS

Sources & evidence

ORD record: ord-3b461c8ed6bb4ff1ba967eb0b9d08034
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491710B2

Reaction notes

Loading…