Cesium carbonate → 6-chloro-5-[4-(propan-2-yl)phenyl]-1H-indole-3-carbaldehyde

HRID 1054880Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][CH:6]=[C:5]2[CH:12]=[O:13].[CH:14]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)([CH3:16])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[Cl:11][C:10]1[CH:9]=[C:8]2[C:4]([C:5]([CH:12]=[O:13])=[CH:6][NH:7]2)=[CH:3][C:2]=1[C:20]1[CH:21]=[CH:22][C:17]([CH:14]([CH3:16])[CH3:15])=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A vial was charged with 1 mL of a 0.1M solution of 5-bromo-6-chloro-1H-indole-3-carbaldehyde (100 uM) in dioxane, 150 umol of (4-isopropylphenyl)boronic acid solution in dioxane, 200 uL of a 1.0M cesium carbonate solution in water, and 1,1′-bis(di-tert-butylphosphino) ferrocene palladium dichloride), (2 umol, 0.02 eq). The vial was purged with nitrogen, sealed and heat to 100° C. for 16 h. The solvent was evaporated and the vial diluted with ethyl acetate. The organic layer was collected, washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to give the title compound.

Workup

customThe vial was purged with nitrogen
customsealed
customThe solvent was evaporated
additionthe vial diluted with ethyl acetate
customThe organic layer was collected
washwashed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-65f72de4985f4265ae45932cac68f148
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394285B2

Reaction notes

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