Water → 8-(Benzyloxy)-2-(7-(2-methoxyethoxy)-imidazo[1,2-a]pyridin-3-yl)quinoline

HRID 1095705Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16](Cl)[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][O:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][N:28]2[CH:31]=[CH:32][N:33]=[C:27]2[CH:26]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1.O>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([C:31]1[N:28]3[CH:29]=[CH:30][C:25]([O:24][CH2:23][CH2:22][O:21][CH3:20])=[CH:26][C:27]3=[N:33][CH:32]=1)[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

8-(Benzyloxy)-2-chloroquinoline (5.0 g, 18.5 mmol), 7-(2-methoxyethoxy)-imidazo[1,2-a]pyridine (3.56 g, 18.5 mmol), Pd(PPh3)4 (1.07 g, 0.927 mmol), K2CO3 (5.12 g, 37.1 mmol), and Pd(OAc)2 (0.208 g, 0.927 mmol) were added into dioxane (74.1 ml, 18.5 mmol) and water (0.735 ml, 40.8 mmol) and heated to 100° C. overnight under nitrogen. The reaction was diluted with DCM and carbon (5 g) was added, followed by filtration. The filtrate was concentrated and then triturated with 1:1 EtOAc/MTBE (30 mL). The resulting solids were allowed to stir for 5 hours and then filtered to isolate of the desired product as a solid (5.4 g, 69% yield).

Workup

additionwas added
filtrationfollowed by filtration
concentrationThe filtrate was concentrated
customtriturated with 1:1 EtOAc/MTBE (30 mL)
filtrationfiltered

Sources & evidence

ORD record: ord-d24a19fa3df546af901b43d1c199f0d9
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138181B2

Reaction notes

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