1H-Indazole-1-propanoic acid synthesis

3synthesis methods

Product Name:1H-Indazole-1-propanoic acid
CAS Number:247128-24-1
Molecular formula:C10H10N2O2
Molecular Weight:190.2

1H-Pyrrole-2,5-dione, 3-[1-(3-hydroxypropyl)-1H-indazol-3-yl]-4-[1-(3-pyridinyl)-1H-indol-3-yl]-

436161-39-6
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87413-09-0
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247128-24-1
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Yield:247128-24-1 98%

Reaction Conditions:

with sodium thiosulfate in dichloromethane;water;

Steps:

34 1H-indazole-1-propanoic acid, 3-[2,5-dihydro-2,5-dioxo-4-[1-(3-pyridinyl)-1H-indol-3-yl]-1H-pyrrol-3-yl]-1H-pyrrole-2,5-dione (Compound 113)

1H-indazole-1-propanoic acid, 3-[2,5-dihydro-2,5-dioxo-4-[1-(3-pyridinyl)-1H-indol-3-yl]-1H-pyrrol-3-yl]-1H-pyrrole-2,5-dione (Compound 113) Dess-Martin reagent (0.34 g, 0.80 mmol) was added to Compound 94 (prepared in Example 28) (0.31 g, 0.664 mmol) in CH₂Cl₂ (12 mL). The mixture was stirred at rt for 3 h, then another portion of Dess-Martin reagent (50 mg, 0.12 mmol) was added and the mixture was stirred for 1 h until TLC showed that Compound 94 was no longer present. The reaction was quenched with 25% Na₂S₂O₃ in water (3 mL). The aqueous layer was extracted with chloroform several times. The organic layers were combined and washed with water and brine, then dried (Na₂SO₄) and evaporated in vacuo to a reddish solid. The solid was purified by flash column chromatography (95:5:0.5; DCM:MeOH:NH₄OH) to afford Compound 112 (300 mg, 98%) as a red solid. ¹H NMR (CD₃OD) δ9.43 (s, 1H), 8.84 (d, J=2.4 Hz, 1H), 8.65 (d, J=4.8 Hz, 1H), 8.26 (s, 1H), 8.12 (m, 1H), 7.70 (m, 1H), 7.61 (m, 2H), 7.43 (m, 2H), 7.14 (m, 2H), 6.75 (t, J=7.5 Hz, 1H), 6.43 (d, J=8.1 Hz, 1H), 4.46 (t, J=6.9 Hz, 2H), 1.96 (m, 2H). ES-MS m/z 462 (MH⁺).

References:

US2003/55097,2003,A1

271-44-3 Synthesis

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247128-24-1
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References

23300-94-9 Synthesis

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247128-24-1
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References