(Pyrimidin-5-yl)boronic acid → HCID 72203013, compound

HRID 629065Notes

Reaction equation

HRID 629065 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]=[C:27](B(O)O)[CH:26]=[N:25][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:27]1[CH:28]=[N:23][CH:24]=[N:25][CH:26]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 89907516HCID 89907516, compound

Product 1

HCID 72203013HCID 72203013, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 1 using 3-iodo-4-methyl-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 13.1) and pyrimidin-5-ylboronic acid to afford a yellow oil. UPLC-MS (Condition 1) tR=2.62 min, m/z=374.0 [M+H]+, m/z=372.0 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.36 (s, 3H) 7.37 (d, J=8.6 Hz, 2H) 7.55 (d, J=8.1 Hz, 1H) 7.88 (d, J=9.0 Hz, 2H) 7.95 (s, 1H) 7.98 (d, J=8.1 Hz, 1H) 8.97 (s, 2H) 9.26 (s, 1H) 10.40 (s, 1H).

Workup

  1. customto afford a yellow oil

Sources & evidence

ORD record
ord-312a0f146784417095d9df697af8ff27
Source dataset
uspto-grants-2016_04
Patent number
US09315489B2

Reaction notes

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