Phenylboronic Acid → HCID 178518847, compound

HRID 855656Notes

Reaction equation

HRID 855656 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([NH:9][C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17](I)[CH:18]=4)[N:13]=[C:12]([NH:21][C:22]4[CH:30]=[C:29]5[C:25]([C:26](=[O:31])[NH:27][NH:28]5)=[CH:24][CH:23]=4)[N:11]=3)[NH:7][N:8]=2)[CH2:3][CH2:2]1.[C:32]1(B(O)O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CS(C)=O.C1([O-])C=CC=CC=1.[K+].O>[CH:1]1([C:4]2[CH:5]=[C:6]([NH:9][C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[CH:18]=4)[N:13]=[C:12]([NH:21][C:22]4[CH:30]=[C:29]5[C:25]([C:26](=[O:31])[NH:27][NH:28]5)=[CH:24][CH:23]=4)[N:11]=3)[NH:7][N:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 66827Phenylboronic AcidHCID 1785188486-[4-(5-Cyclopropyl-2H-pyrazol-3-ylamino)-6-iodo-quinazolin-2-ylamino]-1,2-dihydro-indazol-3-one

Product 1

HCID 178518847HCID 178518847, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 23670670Potassium phenoxideSolvent

Conditions

Temperature
100 °C

Procedure

To 6-[4-(5-Cyclopropyl-2H-pyrazol-3-ylamino)-6-iodo-quinazolin-2-ylamino]-1,2-dihydro-indazol-3-one (300 mg, 0.48 mmol), and phenyl boronic acid (88 mg, 0.72 mmol) in DMSO and 1.5 M potassium phenolate (2.6 mL) was added PdCl2 (dppf)2 (175 mg) and the solution was heated to 100° C. in a sealed tube. After 12 hr, the solution was diluted with water, extracted with ethyl acetate, dried (Na2SO4) and concentrated. The title compound was isolated by preparative HPLC as a white solid (0.82 mg). HPLC tr=5.14 min (10% to 90% MeCN over 8 min, total time 12 min, 3×150 mm C18 column) FIA m/e 475.55 (M+H), 473.55 (M−H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5c20a52e39044b38a73c003a7a67947e
Source dataset
uspto-grants-2007_08
Patent number
US07262200B2

Reaction notes

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