2-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-Indazole → HCID 136177464, compound

HRID 1972861Notes

Reaction equation

HRID 1972861 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8](Br)[CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([O:18][CH3:19])[CH:12]=3)[N:6]2[N:5]=[CH:4][N:3]=1.[CH2:21]([N:28]1[CH:36]=[C:35]2[C:30]([CH:31]=[C:32](B3OC(C)(C)C(C)(C)O3)[CH:33]=[CH:34]2)=[N:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[NH2:1][C:2]1[C:7]2=[C:8]([C:32]3[CH:33]=[CH:34][C:35]4[C:30]([CH:31]=3)=[N:29][N:28]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:36]=4)[CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([O:18][CH3:19])[CH:12]=3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 585293132-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-IndazoleHCID 136351085HCID 136351085, compound

Product 1

HCID 136177464HCID 136177464, compoundYield 9%

Procedure

Using a procedure similar to that of Example 4 with 4-(4-Amino-5-bromo-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-2-methoxy-phenol and 2-benzyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2H-indazole as starting materials, 21.5 mg (9%) of the desired product was isolated. 1H NMR (300 MHz, DMSO-d6) δ 8.80 (s, 1 H), 8.05 (d, 2 H), 8.0 (s, 1 H), 7.90 (d, 1 H), 7.70 (s, 1 H), 7.60-7.40 (m, 7 H), 7.25 (d, 1 H), 7.20 (s, 1 H), 5.70 (s, 2 H), 3.80 (s, 3 H); ES-MS m/z 463.49 [M+H]+, HPLC RT (min) 2.99.

Sources & evidence

ORD record
ord-487e6f141b50467781745df1a41a630f
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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