Formic Acid → HCID 18313597, compound

HRID 277083Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([NH2:8])[N:5]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[N:11]=[C:4]2[CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].C(O)=O.O1[CH2:32][CH2:31][O:30][CH2:29]C1>[CH-]1C=C(P(C2C=CC=CC=2)C2C=CC=CC=2)C=C1.[CH-]1C=C(P(C2C=CC=CC=2)C2C=CC=CC=2)C=C1.Cl[Pd]Cl.[Fe+2]>[CH3:29][O:30][C:31]1[CH:32]=[CH:4][C:3]([C:2]2[CH:7]=[C:6]([NH2:8])[N:5]3[N:9]=[C:10]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=4)[N:11]=[C:4]3[CH:3]=2)=[CH:2][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 72.5 mg (0.25 mmol) 7-bromo-2-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine, 37.4 mg (0.275 mmol) p-methoxy-boronic acid, and 0.22 ml 2M Na2CO3 in 0.78 ml dioxane was treated with 0.05 eq. dichloro (1,1′-bis(diphenylphosphino) ferrocene)palladium (II) dichloromethane adduct and heated to 100° C. for 15 h. Formic acid was added and the mixture was purified by reversed phase column chromatography eluting with an acetonitrile/water gradient yielding 13.3 mg (17%) of the title compound. MS m/e (%): 318 (M+H+, 100)

Workup

customthe mixture was purified by reversed phase column chromatography
washeluting with an acetonitrile/water gradient

Sources & evidence

ORD record: ord-1a95dd4fc8524259a4ad1ce44f7bd2f1
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06355653B1

Reaction notes

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