Oxindole → HCID 178517058, compound

HRID 1615245Notes

Reaction equation

[I:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=O)=[CH:8][CH:9]=2)[NH:4][N:3]=1.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][C:14]1=[O:22]>>[I:1][C:2]1[C:10]2[C:5](=[CH:6][C:7](/[CH:11]=[C:15]3/[C:14](=[O:22])[NH:13][C:21]4[C:16]/3=[CH:17][CH:18]=[CH:19][CH:20]=4)=[CH:8][CH:9]=2)[NH:4][N:3]=1

Participants

Reactant 2

HCID 321710Oxindole

HCID 178519327HCID 178519327, compound

Product 1

HCID 178517058HCID 178517058, compound

Procedure

The title compound was synthesized from 3-iodo-1H-indazole-6-carbaldehyde (15 mg, 0.0551 mmol) and oxindole (8 mg, 0.0616 mmol) according to the method described for Example A11B and purified by column chromatography (silica gel, CH2Cl2/MeOH, 98:2 to 96:4) to obtain 6.9 mg, 33% of a yellow solid. 1H NMR (400 MHz, CD3OD) δ 7.89-7.82 (m, 2H), 7.63-7.49 (m, 3H), 7.23 (t, J=8.21 Hz, 1H), 6.91 (d, J=7.07 Hz, 1H), 6.89-6.83 (m, 1H); MS ESI 388.0 [M+H]+, calcd for [C16H10IN3O+H]+ 387.99.

Workup

custompurified by column chromatography (silica gel, CH2Cl2/MeOH, 98:2 to 96:4)

Sources & evidence

ORD record: ord-05c07b1af00642e78fd9dfda57c7af94
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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