1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 178480029, compound

HRID 2103720Notes

Reaction equation

HRID 2103720 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([C@H:9]3[CH2:12][C@H:11]([N:13]4[CH2:17][CH2:16][CH2:15][C@H:14]4[CH3:18])[CH2:10]3)[S:8][C:4]=2[CH:3]=1.[CH3:21][N:22]1[CH:26]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:24]=[N:23]1.N1C=C(B(O)O)C=N[CH:37]=1>>[N:13]1([C@H:11]2[CH2:12][C@H:9]([C:7]3[S:8][C:4]4[CH:3]=[C:2]([C:25]5[CH:24]=[N:23][N:22]([CH3:21])[CH:26]=5)[CH:20]=[CH:19][C:5]=4[N:6]=3)[CH2:10]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:18][CH2:37]1

Participants

4

Reactant 3

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 178461421HCID 178461421, compound

Product 1

HCID 178480029HCID 178480029, 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 1-methyl-4-1H-pyrazoleboronic acid pinacol ester for pyrimidine-5-boronic acid. 1H NMR (500 MHz, CDCl3) δ ppm 7.89-7.97 (m, 2H) 7.80 (s, 1H) 7.65 (s, 1H) 7.55 (dd, J=8.39, 1.68 Hz, 1H) 3.97 (s, 3H) 3.74-3.83 (m, 1H) 3.30-3.41 (m, 1H) 2.46-2.61 (m, 8H) 1.56-1.71 (m, 8H). MS: (M+H)+=367.

Sources & evidence

ORD record
ord-adb76a705c7e40c19a23ef3164419acd
Source dataset
uspto-grants-2009_08
Patent number
US07576110B2

Reaction notes

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