(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 472538Notes

Reaction equation

HRID 472538 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)+.

Sources & evidence

ORD record
ord-a48a5711a5d2430b8ab9d7f968f9f52e
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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