3-Tolylboronic acid → HCID 10362431, compound

HRID 2373502Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[C:10]([C:18](=[O:22])[C:19](O)=[O:20])=[C:9]1[CH2:23][OH:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K].[C:26]1([CH3:35])[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([CH3:35])[CH:27]=3)=[CH:14][CH:15]=2)[C:10]2[C:18](=[O:22])[C:19](=[O:20])[O:24][CH2:23][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 27339503-Tolylboronic acid

HCID 5462222Potassium

HCID 21964311HCID 21964311, compound

Product 1

HCID 10362431HCID 10362431, compound

Procedure

The title compound was prepared from [1-benzyl-5-bromo-2-(hydroxymethyl)-1H-indol-3-yl](oxo)acetic acid, potassium salt and m-tolylboronic acid in substantially the same manner, as described in step 4 of Example 9. The product was obtained as a grey solid, mp: 225-226° C.; Mass spectrum (ESI, [M+H]+) m/z 382. 1H-NMR (400 MHz, DMSO-d6) δ 8.22 (s, 1H), 7.22 (d, 1H, J=8.40 Hz), 7.65 (dd, 1H, J=8.45 and 1.83 Hz), 7.49 (s, 1H), 7.47-7.34 (m, 3H), 7.31 (d, 1H, J=7.33 Hz), 7.27 (d, 2H, J=8.40 Hz), 7.18 (d, 1H, J=7.48 Hz), 5.92 (s, 2H), 5.55 (s, 2H), and: 2.39 ppm (s, 3H).

Workup

customThe product was obtained as a grey solid, mp: 225-226° C.

Sources & evidence

ORD record: ord-735373be3a3e4ff0bdaa66a7a691df75
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459478B2

Reaction notes

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