1-Methyl-2-(tributylstannyl)-1H-imidazole → HCID 67492166, compound

HRID 1922082Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:27][CH:28]([F:30])[F:29])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.[CH3:32][N:33]1[CH:37]=[CH:36][N:35]=[C:34]1[Sn](CCCC)(CCCC)CCCC>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.O1CCOCC1>[CH3:1][O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:27][CH:28]([F:30])[F:29])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:34]3[N:33]([CH3:32])[CH:37]=[CH:36][N:35]=3)=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of [3-(4-bromobenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic acid methyl ester (0.22 g), 1-methyl-2-tributylstannanyl-1H-imidazole (0.50 g), tetrakis(triphenylphosphine)palladium(0) (0.055 g) and 1,4-dioxane (4.4 mL) was heated at 100° C. for 1 hour. The mixture was cooled to room temperature and used in the next step.

Workup

temperatureThe mixture was cooled to room temperature

Sources & evidence

ORD record: ord-b7a0183e1f204fd9a78fd322b8a7be61
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173812B2

Reaction notes

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