Sodium Bicarbonate → HCID 136055992, compound

HRID 1726081Notes

Reaction equation

HRID 1726081 reaction equation
C([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1B(O)O)(OC(C)(C)C)=O.C(=O)(O)[O-].[Na+].C(OC([N:28]1[C:36]2[C:31](=[CH:32][C:33]([P:37]([O:41]C)([O:39][CH3:40])=[O:38])=[CH:34][CH:35]=2)[C:30](I)=[N:29]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>[CH3:40][O:39][P:37]([C:33]1[CH:32]=[C:31]2[C:36](=[CH:35][CH:34]=1)[NH:28][N:29]=[C:30]2[C:9]1[NH:8][CH:12]=[CH:11][CH:10]=1)(=[O:38])[OH:41]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 57562495HCID 57562495, compound

Product 1

HCID 136055992HCID 136055992, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

44.8 mg (0.25 eq; 0.039 mmol) of tetrakis(triphenylphosphine)palladium(0), 65.3 mg (2 eq; 0.310 mmol) of 1-boc-pyrrole-2-boronic acid, 3 ml of dimethylformamide and 150 μl of saturated sodium bicarbonate solution are added to 70 mg (1 eq; 0.155 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 4.10 mg of ([3-(1H-pyrrol-2-yl)-1H-indazol-5-yl]-phosphonic acid monomethyl ester.

Workup

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

Sources & evidence

ORD record
ord-901cf589055f4ba891532be412db7341
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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