3-Pyridinylboronic acid → HCID 89906547, compound

HRID 629066Notes

Reaction equation

HRID 629066 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6].[N:23]1[CH:28]=[CH:27][CH:26]=[C:25](B(O)O)[CH:24]=1>>[CH3:22][C:21]1[CH:20]=[CH:19][C:4]([C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)=[O:6])=[CH:3][C:2]=1[C:25]1[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 89907516HCID 89907516, compound

Product 1

HCID 89906547HCID 89906547, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 13 using 3-iodo-4-methyl-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 13.1) and pyridin-3-ylboronic acid to afford a yellow oil. UPLC-MS (Condition 1) tR=2.27 min, m/z=373.0 [M+H]+, m/z=371.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.32 (s, 3H) 7.36 (d, J=8.6 Hz, 2H) 7.49-7.55 (m, 2H) 7.83-7.92 (m, 2H) 7.83-7.92 (m, 2H) 7.94 (dd, J=7.8, 1.7 Hz, 1H) 8.63 (dd, J=4.8, 1.3 Hz, 1H) 8.67 (d, J=1.7 Hz, 1H) 10.37 (s, 1H).

Workup

  1. customto afford a yellow oil

Sources & evidence

ORD record
ord-f7018f91bcdb428c8630e16f0d0ce878
Source dataset
uspto-grants-2016_04
Patent number
US09315489B2

Reaction notes

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