Ethyl 3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxylate → 3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxylic acid

HRID 1467303Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]([O:18]CC)=[O:17])[CH:14]=3)[N:9]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:8]=2)=[CH:3][CH:2]=1>C1COCC1>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=3)[N:9]([C:21]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:8]=2)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a 5 ml microwave vial equipped with a stir bar was added ethyl 3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxylate (816 mg, 1.601 mmol), LOH (2402 μl, 2.402 mmol), and THF (8006 μl). The vial was sealed and heated to 50° C. for 19 hours, after which the LCMS indicates formation of the desired product. Crude was quenched with HCl (2402 μl, 2.402 mmol) and the reaction was concentrated in vacuo. Material was dry loaded onto a 100 g column; was run from 100% dichloromethane to 25% methanol. Desired product eluted; fractions were collected and concentrated in vacuo to a white solid.

Workup

customTo a 5 ml microwave vial equipped with a stir bar
customThe vial was sealed

Sources & evidence

ORD record: ord-af79fa19069d425faa2a83b5e963b6eb
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999957B2

Reaction notes

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