(2,2-Difluoro-1,3-dioxaindan-4-yl)boronic acid → 2,2-Difluoro-1,3-benzodioxol-4-yl-[1,2,4]triazolo[1,5-a]pyridine

HRID 1890010Notes

Reaction equation

HRID 1890010 reaction equation
Br[C:2]1[C:3]2[N:4]([N:8]=[C:9](Cl)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[F:12][C:13]1([F:25])[O:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:21](B(O)O)[C:15]=2[O:14]1>>[F:25][C:13]1([F:12])[O:14][C:15]2[CH:21]=[CH:20][CH:19]=[C:18]([C:9]3[N:10]=[C:3]4[CH:2]=[CH:7][CH:6]=[CH:5][N:4]4[N:8]=3)[C:16]=2[O:17]1

Participants

3

Reactant 2

HCID 16427145(2,2-Difluoro-1,3-dioxaindan-4-yl)boronic acidHCID 674813708-Bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 866483612,2-Difluoro-1,3-benzodioxol-4-yl-[1,2,4]triazolo[1,5-a]pyridine

Procedure

2-Chloro-8-(2,2-difluoro-1,3-benzodioxol-4-yl-[1,2,4]triazolo[1,5-a]pyridine was prepared from 8-bromo-2-chloro[1,2,4]triazolo[1,5-a]pyridine (0.71 g, 3.0 mmol) and 2,2-difluorobenzo[1,3]dioxole-4-boronic acid (0.64 g, 3.2 mmol) in a manner analogous to Example 2c. Product was isolated as a foam (0.63 g, 67%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.84 (d, J=7.5 Hz, 1H), 7.78-7.67 (m, 2H), 7.33-7.23 (m, 2H), 7.36 (d, J=6 Hz, 1H), MS=310 (MH)+. 243b) 7-[8-(2,2-difluoro-1,3-benzodioxol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl-amino]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester was prepared from 2-chloro-8-(2,2-difluoro-1,3-benzodioxol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine (0.78 g, 2.5 mmol), and 7-amino-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester (0.99 g, 3.778 mmol), in a manner analogous to Example 2d. Product was isolated as a foam (0.78 g, 58%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.48 (d, J=6 Hz, 1H), 7.61 (d, J=6 Hz, 1H), 7.51-7.42 (m, 4H), 7.00-6.89 (m, 3H), 6.79 (s, 1H), 3.62-3.45 (m, 4H), 2.84-2.74 (m, 4H), 1.52 (s, 9H). MS=536 (MH)+.

Sources & evidence

ORD record
ord-d1936f3660884c39a9633b1a728c0ce1
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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