Oxindole → (3E)-3-(1H-indazol-6-ylmethylidene)-1H-indol-2-one

HRID 1410343Notes

Reaction equation

HRID 1410343 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][C:7](/[CH:11]=[C:12]3/[C:13](=[O:21])[NH:14][C:15]4[C:20]/3=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:8][CH:9]=2)[NH:4][N:3]=1.N1C2C(=CC=CC=2)CC1=O.N1C2C(=CC=C(C=O)C=2)C=N1>>[NH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7](/[CH:11]=[C:12]3/[C:13](=[O:21])[NH:14][C:15]4[C:20]/3=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:6]=2)[CH:2]=[N:3]1

Participants

4

Reactant 3

HCID 321710OxindoleHCID 185383681H-Indazole-6-carbaldehydeHCID 178517058HCID 178517058, compound

Product 1

HCID 178517060(3E)-3-(1H-indazol-6-ylmethylidene)-1H-indol-2-oneYield 51%

Procedure

According to the method described for (E)-3-((3-iodo-1H-indazol-6-yl)methylene)-indolin-2-one, oxindole (67 mg, 0.216 mmol) and 1H-indazole-6-carbaldehyde (73 mg, 0.238 mmol) gave (E)-3-((1H-indazol-6-yl)methylene)indolin-2-one (32 mg, 51%). 1H NMR (400 MHz, CD3OD) δ 8.14 (s, 1H), 7.91 (d, J=8.5 Hz, 1H), 7.89 (s, 2H), 7.65 (d, J=7.6 Hz, 1H), 7.47 (d, J=8.4 Hz, 1H), 7.25 (t, J=7.7 Hz, 1H), 6.93 (d, J=7.8 Hz, 1H), 6.87 (t, J=7.6 Hz, 1H); MS ESI 262.0 [M+H]+, calcd for [C16H11N3O+H]+ 262.10.

Sources & evidence

ORD record
ord-d84b748b15e24fa8ac5b1e57d2e0d2df
Source dataset
uspto-grants-2014_12
Patent number
US08921545B2

Reaction notes

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