Dichloromethane → HCID 59432313, compound

HRID 507086Notes

Reaction equation

[C:1](=O)([O-])[O-].[Cs+].[Cs+].CB(O)O.ClCCl.[CH:14]([O:17][C:18]([N:20]1[C:26]2[C:27]3[CH2:28][CH2:29][CH2:30][C:31]=3[C:32](Br)=[CH:33][C:25]=2[C@@H:24]([NH:35][CH2:36][C:37]2[CH:42]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:40]=[C:39]([C:47]([F:50])([F:49])[F:48])[CH:38]=2)[CH2:23][CH2:22][CH2:21]1)=[O:19])([CH3:16])[CH3:15]>O1CCOCC1>[CH:14]([O:17][C:18]([N:20]1[C:26]2[C:27]3[CH2:28][CH2:29][CH2:30][C:31]=3[C:32]([CH3:1])=[CH:33][C:25]=2[C@@H:24]([NH:35][CH2:36][C:37]2[CH:42]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:40]=[C:39]([C:47]([F:50])([F:49])[F:48])[CH:38]=2)[CH2:23][CH2:22][CH2:21]1)=[O:19])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 110 °C

Procedure

Add cesium carbonate (383 mg, 2.52 mmol), methyl boronic acid (76 mg, 1.26 mmol) and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (69 mg, 0.084 mmol) to a solution of (S)-6-(3,5-bis-trifluoromethyl-benzylamino)-4-bromo-2,3,6,7,8,9-hexahydro-1H-10-aza-cyclohepta[e]indene-10-carboxylic acid isopropyl ester (500 mg, 0.84 mmol) in dioxane (7 mL). Stir the mixture under nitrogen at 110° C. for 2 h. Cool down the mixture to room temperature and filter over Celite® washing with dichloromethane. Evaporate the solvent and purify the crude by chromatography, eluting with hexane/ethyl acetate (90/10) to afford the title compound (355 mg, 0.67 mmol, 80%). MS (ES+): 529 (M+H).

Workup

temperatureCool down the mixture to room temperature
filtrationfilter over Celite®
washwashing with dichloromethane
customEvaporate the solvent
custompurify the crude by chromatography
washeluting with hexane/ethyl acetate (90/10)

Sources & evidence

ORD record: ord-59cdeee0093742aeac52122fb5928145
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786108B2

Reaction notes

Loading…