(Pyrimidin-5-yl)boronic acid → HCID 178423685, compound

HRID 2047562Notes

Reaction equation

HRID 2047562 reaction equation
[N:1]1([C@H:5]2[CH2:8][C@H:7]([C:9]3[S:10][C:11]4[CH:17]=[C:16](Br)[CH:15]=[CH:14][C:12]=4[N:13]=3)[CH2:6]2)[CH2:4][CH2:3][CH2:2]1.BrC1C=CC2N=C([C@H]3[CH2:30][C@H:29]([N:31]4[CH2:35][CH2:34][CH2:33][C@H:32]4[CH3:36])C3)SC=2C=1.CC1C(B2OC(C)(C)C(C)(C)O2)=CC=C(C)N=1.N1C=C(B(O)O)C=NC=1>>[N:1]1([C@H:5]2[CH2:8][C@H:7]([C:9]3[S:10][C:11]4[CH:17]=[C:16]([C:35]5[C:29]([CH3:30])=[N:31][C:32]([CH3:36])=[CH:33][CH:34]=5)[CH:15]=[CH:14][C:12]=4[N:13]=3)[CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 219800342,6-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 178419315HCID 178419315, compoundHCID 178461421HCID 178461421, compound

Product 1

HCID 178423685HCID 178423685, compound

Procedure

The title compound was prepared according to the procedure described in Example 1F, except for substituting the product of Example 61A for the product of Example 1E, and substituting Example 2A (2,6-dimethyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine) for pyrimidine-5-boronic acid. 1H NMR (300 MHz, CDCl3) δ ppm 8.01 (d, J=8.48 Hz, 1H) 7.75 (d, J=1.36 Hz, 1H) 7.45 (d, J=7.80 Hz, 1H) 7.39 (dd, J=8.48, 1.70 Hz, 1H) 7.06 (d, J=7.80 Hz, 1H) 3.96-4.08 (m, 1H) 3.19-3.40 (m, 5H) 2.59 (s, 3H) 2.49 (s, 3H) 2.37-2.56 (m, 4H) 2.07-2.19 (m, 2H). MS: (M+H)+=350.

Sources & evidence

ORD record
ord-d85f821fb1fb4c99828b37848cdc8007
Source dataset
uspto-grants-2013_11
Patent number
US08592467B2

Reaction notes

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