(Pyrimidin-5-yl)boronic acid → HCID 178423688, compound

HRID 2103719Notes

Reaction equation

HRID 2103719 reaction equation
[N:1]1([C@H:8]2[CH2:11][C@H:10]([C:12]3[S:13][C:14]4[CH:20]=[C:19](Br)[CH:18]=[CH:17][C:15]=4[N:16]=3)[CH2:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.BrC1C=CC2N=C([C@H]3[CH2:33][C@H:32]([N:34]4[CH2:38][CH2:37][CH2:36][C@H:35]4[CH3:39])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:8]2[CH2:11][C@H:10]([C:12]3[S:13][C:14]4[CH:20]=[C:19]([C:38]5[C:32]([CH3:33])=[N:34][C:35]([CH3:39])=[CH:36][CH:37]=5)[CH:18]=[CH:17][C:15]=4[N:16]=3)[CH2:9]2)[CH2:7][CH2:6][CH2:5][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 178419318HCID 178419318, compoundHCID 178461421HCID 178461421, compound

Product 1

HCID 178423688HCID 178423688, compound

Procedure

The title compound was prepared according to the procedure described in Example 1F, except for substituting the product of Example 71A 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 (500 MHz, CDCl3) δ ppm 8.02 (d, J=8.54 Hz, 1H) 7.76 (d, J=1.53 Hz, 1H) 7.46 (d, J=7.63 Hz, 1H) 7.39 (dd, J=8.24, 1.83 Hz, 1H) 7.07 (d, J=7.63 Hz, 1H) 3.78-3.86 (m, 1H) 3.32-3.43 (m, 1H) 2.59 (s, 6H) 2.45-2.56 (m, 8H) 1.58-1.73 (m, 8H). MS: (M+H)+=392.

Sources & evidence

ORD record
ord-2bbca304abd94df2988ddf8c91d4536a
Source dataset
uspto-grants-2009_08
Patent number
US07576110B2

Reaction notes

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