6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(3,2-b)pyridine → 4-amino-7-methyl-8-(1H-pyrrolo[3,2-b]pyridin-6-yl)cinnoline-3-carboxamide

HRID 2203225Notes

Reaction equation

HRID 2203225 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[NH:17][CH:16]=[CH:15][C:12]3=[N:13][CH:14]=2)O1.[NH2:19][C:20]1[C:29]2[C:24](=[C:25](Br)[C:26]([CH3:30])=[CH:27][CH:28]=2)[N:23]=[N:22][C:21]=1[C:32]([NH2:34])=[O:33]>>[NH2:19][C:20]1[C:29]2[C:24](=[C:25]([C:9]3[CH:10]=[C:11]4[NH:17][CH:16]=[CH:15][C:12]4=[N:13][CH:14]=3)[C:26]([CH3:30])=[CH:27][CH:28]=2)[N:23]=[N:22][C:21]=1[C:32]([NH2:34])=[O:33]

Participants

3

Reactant 2

HCID 242292706-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(3,2-b)pyridineHCID 898252134-Amino-8-bromo-7-methylcinnoline-3-carboxamide

Product 1

HCID 898334644-amino-7-methyl-8-(1H-pyrrolo[3,2-b]pyridin-6-yl)cinnoline-3-carboxamide

Procedure

The title compound was prepared in a manner similar to EXAMPLE 1 using 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[3,2-b]pyridine and 4-amino-8-bromo-7-methylcinnoline-3-carboxamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.40 (s, 3H), 6.84 (br s, 1 H), 6.93 (br s, 1 H), 7.85 (d, J=8.59 Hz, 1 H), 8.15 (br s, 1 H), 8.27-8.30 (m, 1 H), 8.35 (s, 1 H), 8.54 (d, J=8.59 Hz, 1 H), 8.58 (s, 1 H), 8.71 (br s, 1 H), 8.76 (s, 1 H); ESI-MS m/z [M+H]+ 319.2.

Sources & evidence

ORD record
ord-b2f2ffad71c94bca8eac86413b356b64
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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