Water → HCID 69416361, compound

HRID 1270162Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([NH:17][CH:18]([CH3:20])[CH3:19])[C:8]3[N:9]2[C:12]([O:15]C)=[N:13][N:14]=3)=[CH:4][CH:3]=1.[C:21]1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH3:57][OH:58].CS(C)=O.[OH2:63]>C(Cl)Cl>[CH3:57][O:58][C:21]([C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([NH:17][CH:18]([CH3:20])[CH3:19])[C:8]3[N:9]2[C:12](=[O:15])[NH:13][N:14]=3)=[CH:4][CH:3]=1)=[O:63]

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of 2.0 g of (8-bromo-1-methoxy-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)-isopropyl-amine, 0.54 g of Pd(II)acetate, 0.66 g of 1,3-bis-(diphenylphosphino)propane, and triethylamine (21 mL) in a 1.1/1.0 mixture of MeOH/DMSO was agitated under an atmosphere of CO (45 psi) at 75° C. for 96 hrs. After cooling to 23° C., the solution was diluted with water and methylene chloride and the resulting mixture filtered through diatomaceous earth. The filtrate was concentrated and the residue was dissolved in methylene chloride and washed with brine (2×). The title compound precipitated from the organic layer upon standing and was isolated by filtration. MS (M+H)+=302.3.

Workup

temperatureAfter cooling to 23° C.
filtrationthe resulting mixture filtered through diatomaceous earth
concentrationThe filtrate was concentrated
dissolutionthe residue was dissolved in methylene chloride
washwashed with brine (2×)
customThe title compound precipitated from the organic layer
customwas isolated by filtration

Sources & evidence

ORD record: ord-cd5b2c331dfc436d81f548adeab09221
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202245B2

Reaction notes

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