Sodium Bicarbonate → HCID 136055974, compound

HRID 1726079Notes

Reaction equation

C([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1B(O)O)(OC(C)(C)C)=O.C(=O)(O)[O-].[Na+].C(OC([N:32]1[C:40]2[C:35](=[CH:36][C:37]([P:41]([O:45]C)([O:43][CH3:44])=[O:42])=[CH:38][CH:39]=2)[C:34](I)=[N:33]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>[CH3:44][O:43][P:41]([C:37]1[CH:36]=[C:35]2[C:40](=[CH:39][CH:38]=1)[NH:32][N:33]=[C:34]2[C:9]1[NH:8][C:16]2[C:11]([CH:10]=1)=[CH:12][CH:13]=[CH:14][CH:15]=2)(=[O:42])[OH:45]

Participants

Conditions

Temperature: 130 °C

Procedure

82.9 mg (0.25 eq; 0.072 mmol) of tetrakis(triphenylphosphine)palladium(0), 150.1 mg (2 eq; 0.575 mmol) of 1-boc-indole-2-boronic acid, 5 ml of dimethylformamide and 250 μl of saturated sodium bicarbonate solution are added to 130 mg (1 eq; 0.287 mmol) of 5-(dimethoxyphosphoryl)-3-iodo-indazole-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 41 mg of [3-(1H-indol-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-8d56be7a668f481a9556db3906925aa8
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491710B2

Reaction notes

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