(5-Benzyloxy-3-cyano-indazol-1-yl)-acetic acid tert-butyl ester → Tert-butyl 2-(3-cyano-5-(pyrimidin-2-ylmethoxy)-1H-indazol-1-yl)acetate

HRID 1052114Notes

Reaction equation

[C:1]([O:5][C:6](=[O:27])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]3C=CC=CC=3)=[CH:14][CH:15]=2)[C:10]([C:25]#[N:26])=[N:9]1)([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:25]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]3[N:9]=[CH:10][CH:11]=[CH:16][N:8]=3)[CH:12]=2)[N:8]([CH2:7][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:27])[N:9]=1)#[N:26]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of (5-benzyloxy-3-cyano-indazol-1-yl)-acetic acid tert-butyl ester (4 g, 11.01 mmol) in THF (400 mL) was added Pd/Al2O3 (5%) (4.10 g, 38.5 mmol). The reaction mixture was stirred at 40° C. for 16 h under H2 atmosphere (4 bars). The reaction mixture was filtered through a pad of Celite, which was then washed with CH2Cl2. The combined organics were concentrated under vacuum to give the title compound as a yellow solid. MS (LC/MS): 296.0 [M+Na]+; tR (conditions e): 4.46 min.

Workup

filtrationThe reaction mixture was filtered through a pad of Celite, which
washwas then washed with CH2Cl2
concentrationThe combined organics were concentrated under vacuum

Sources & evidence

ORD record: ord-4b10d92000f9498499590a821424a432
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388199B2

Reaction notes

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