4-[(Methylsulfonyl)methyl]phenylboronic acid → 8-(4-Methanesulfonylmethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

HRID 472302Notes

Reaction equation

HRID 472302 reaction equation
Br[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH2:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:12][S:13]([CH2:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)(=[O:15])=[O:14]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:12][S:13]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[C:3]3[N:4]([N:8]=[C:9]([NH2:11])[N:10]=3)[CH:5]=[CH:6][CH:7]=2)=[CH:19][CH:18]=1)(=[O:14])=[O:15]

Participants

4

Reactant 2

HCID 37468194-[(Methylsulfonyl)methyl]phenylboronic acidHCID 468640698-Bromo-(1,2,4)triazolo(1,5-a)pyridin-2-amine

Product 1

HCID 674788568-(4-Methanesulfonylmethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

8-(4-Methanesulfonylmethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine was prepared from 8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (200.0 mg, 0.9388 mmol) and (4-methanesulfonylmethylphenyl)boronic acid (240.0 mg, 1.121 mmol) with Pd(dppf)Cl2 (130.0 mg) as the catalyst in a manner analogous to Step 2c. The reaction product was isolated as a pale yellow solid (0.051 g, 18%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.56 (dd, J=6.6, 1.0 Hz, 1H), 8.12 (d, J=8.3 Hz, 2H), 7.73 (dd, J=7.5, 1.0 Hz, 1H), 7.52 (d, J=8.3 Hz, 2H), 6.99 (dd, J=7.3, 7.3 Hz, 1H), 6.11 (s, 1H), 4.55 (s, 2H), 2.94 (s, 3H). MS=303 (MH)+.

Sources & evidence

ORD record
ord-4614ca9f3c9d4356b208558ccf1977ca
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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