2-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-Indazole → HCID 58529933, compound

HRID 1972870Notes

Reaction equation

HRID 1972870 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([Cl:18])[CH:13]=2)[N:5]2[C:10]=1[C:9]([NH2:11])=[N:8][CH:7]=[N:6]2.[CH2:19]([N:26]1[CH:34]=[C:33]2[C:28]([CH:29]=[C:30](B3OC(C)(C)C(C)(C)O3)[CH:31]=[CH:32]2)=[N:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([N:26]1[CH:34]=[C:33]2[C:28]([CH:29]=[C:30]([C:2]3[CH:3]=[C:4]([C:12]4[CH:17]=[CH:16][N:15]=[C:14]([Cl:18])[CH:13]=4)[N:5]4[C:10]=3[C:9]([NH2:11])=[N:8][CH:7]=[N:6]4)[CH:31]=[CH:32]2)=[N:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 585293132-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-IndazoleHCID 86659603HCID 86659603, compound

Product 1

HCID 58529933HCID 58529933, compoundYield 28%

Procedure

Using a procedure similar to that of Example 4 with 5-bromo-7-(2-chloro-pyridin-4-yl)-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine and 2-benzyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxa-borolan-2-yl)-2H-indazole as starting materials, 60 mg (28%) of the desired product was isolated. 1H NMR (300 MHz, DMSO-d6) δ 8.60 (s, 1 H), 8.5 (d, 2 H), 8.0 (m, 2 H), 7.90 (d, 1 H), 7.70 (s, 1 H), 7.60-7.40 (m, 3 H), 7.25-7.15 (m, 4 H), 7.20 (s, 1 H), 5.70 (s, 2 H); ES-MS m/z 45224 [M+H]+, HPLC RT (min) 3.33.

Sources & evidence

ORD record
ord-864a9e65041c44ed940600e73483a9a7
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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