N-Methyloxindole → HCID 178481478, compound

HRID 1615242Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3]1=[O:11].[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH:21]=O)[CH:19]=2)[CH:14]=[N:13]1>>[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18](/[CH:21]=[C:4]3/[C:3](=[O:11])[N:2]([CH3:1])[C:10]4[C:5]/3=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:19]=2)[CH:14]=[N:13]1

Participants

Reactant 2

HCID 6096N-Methyloxindole

HCID 185383681H-Indazole-6-carbaldehyde

Product 1

HCID 178481478HCID 178481478, compoundYield 17.5%

Procedure

The desired product was synthesized according to the method described for Example A11B, except substituting 1-methylindolin-2-one (37 mg, 0.249 mmol) and 1H-indazole-6-carbaldehyde (40 mg, 0.274 mmol) and then purified by preparatory HPLC to obtain the title compound (12 mg, 17%) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ 8.13 (s, 1H), 7.96-7.86 (m, 3H), 7.67 (d, J=7.83 Hz, 1H), 7.46 (d, J=8.08 Hz, 1H), 7.33 (t, J=7.71 Hz, 1H), 7.02 (d, J=7.83 Hz, 1H), 6.93 (t, J=7.71 Hz, 1H), 3.31 (s, 3H); MS ESI 276.1 [M+H]+, calcd for [C17H13N3O+H]+ 276.11.

Workup

customThe desired product was synthesized
custompurified by preparatory HPLC

Sources & evidence

ORD record: ord-d1a83ef53b19440bae8c78c6a7594e9c
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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