4-(Methylcarbamoyl)benzeneboronic acid → 4-[2-(2-Methoxy-phenylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-yl]-N-methyl-benzamide

HRID 1889753Notes

Reaction equation

HRID 1889753 reaction equation
Br[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][CH3:19])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:20][NH:21][C:22]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)=[O:23]>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]>[CH3:19][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[NH:11][C:9]1[N:10]=[C:3]2[C:2]([C:27]3[CH:28]=[CH:29][C:24]([C:22]([NH:21][CH3:20])=[O:23])=[CH:25][CH:26]=3)=[CH:7][CH:6]=[CH:5][N:4]2[N:8]=1

Participants

4

Reactant 2

HCID 27735264-(Methylcarbamoyl)benzeneboronic acidHCID 67481519(8-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-(2-methoxy-phenyl)-amine

Product 1

HCID 674814324-[2-(2-Methoxy-phenylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-yl]-N-methyl-benzamide

Reagents, catalysts & solvents 1

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

Procedure

4-[2-(2-Methoxy-phenylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-yl]-N-methyl-benzamide was prepared from (8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-(2-methoxy-phenyl)-amine (50.0 mg, 0.157 mmol) and 4-(N-methylaminocarbonyl)phenylboronic acid (31.0 mg, 0.173 mmol) with Pd(dppf)Cl2 (0.012 g) as the catalyst in a manner analogous to Step 2c and was isolated as a pale yellow solid (0.023 g, 39%). MP=275-278° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.48-8.45 (m, 1H), 8.41-8.37 (m, 1H), 8.11 (d, J=8.2 Hz, 2H), 7.91 (d, J=8.2 Hz, 2H), 7.64-7.59 (m, 2H), 7.08-7.02 (m, 1H), 7.00-6.88 (m, 3H), 6.17 (br s, 1H), 3.92 (s, 3H), 3.07 (d, J=4.7 Hz, 3H). MS=374 (MH)+.

Sources & evidence

ORD record
ord-f676228ce6984c8cbe7871800b125d5f
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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