1,1'-Biphenyl-4-yl-boronic acid → HCID 10049054, compound

HRID 2373503Notes

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]([OH:21])=[O:20])=[C:9]1[CH2:23]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K].[C:26]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:38]3[CH:39]=[CH:40][C:35]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:36][CH:37]=3)=[CH:14][CH:15]=2)[C:10]2[C:18](=[O:22])[C:19](=[O:21])[O:20][CH2:23][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 1512531,1'-Biphenyl-4-yl-boronic acid

HCID 5462222Potassium

HCID 21964311HCID 21964311, compound

Product 1

HCID 10049054HCID 10049054, compound

Procedure

The title compound was prepared from [1-benzyl-5-bromo-2-(hydroxymethyl)-1H-indol-3-yl](oxo)acetic acid, potassium salt and 4-biphenylboronic acid in substantially the same manner, as described in step 4 of Example 9. The product was obtained as a white solid, mp: 254-255° C.; Mass spectrum (ESI, [M+H]+) m/z 444. 1H NMR (400 MHz, DMSO-d6) δ 8.26(s, 1H), 7.75-7.68 (m, 8H), 7.45-7.43 (m, 2H), 7.36-7.23 (m, 6H), 5.89 (s, 2H), 5.53 ppm (s, 2H).

Workup

customThe product was obtained as a white solid, mp: 254-255° C.

Sources & evidence

ORD record: ord-85ca2656a0574a8b9ece5f76ebe07ab1
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459478B2

Reaction notes

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