Phenylboronic Acid → 5-Phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 1889815Notes

Reaction equation

Br[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[C:12]1([C:2]2[N:7]3[N:8]=[C:9]([NH2:11])[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Reactant 2

HCID 66827Phenylboronic Acid

HCID 252159395-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 672931715-Phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Procedure

5-Phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine was prepared from 5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (3.00 g, 14.0 mmol) and phenyl boronic acid (1.8 g, 15.0 mmol), in a manner analogous to Step 73c. The product was isolated as a white powder (0.567 g, 19%) after chromatography on an Isco silica gel column (80 g) using methanol in dichloromethane as the eluent. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 7.94 (d, J=6.9 Hz, 2H), 7.52 (m, 4H), 7.37 (m, 1H), 7.02 (d, J=6.5 Hz, 1H), 6.02 (s, 2H). MS=210 (MH)+. 76b) (5-Phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine was prepared from 5-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (100.0 mg, 0.476 mmol) and 1-[2-(4-bromo-phenoxy)-ethyl]-pyrrolidine (119 μl, 0.571 mmol) in a manner analogous to Example 75. The title compound (5-Phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine was isolated as the TFA salt as a off white solid (0.0037 g, 2%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 10.05 (br s, 1H), 9.48 (s, 1H), 8.04 (d, J=8.5 Hz, 2H), 7.61 (m, 7H), 7.18 (d, J=7.5 Hz, 1H), 6.95 (d, J=8.5 Hz, 2H), 4.25 (m, 2H), 3.80-3.40 (m, 4H), 3.12 (m, 2H), 2.03 (m, 2H), 1.89 (m, 2H). MS=400 (MH)+.

Sources & evidence

ORD record: ord-088c422fc49e44899d9d4e7864e4aa7e
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501936B2

Reaction notes

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