Sodium Carbonate → HCID 69313869, compound

HRID 1392714Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[C:11](=[O:18])[C:10]([C:19]([NH:21][CH2:22][CH2:23][S:24][CH3:25])=[O:20])=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.Br[C:27]1[CH:32]=[CH:31][C:30]([C@@H:33]2[CH2:35][C@H:34]2[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:29][CH:28]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)CC.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>[CH3:25][S:24][CH2:23][CH2:22][NH:21][C:19]([C:10]1[C:11](=[O:18])[C:12]2[C:17](=[N:16][CH:15]=[CH:14][CH:13]=2)[N:8]([C:4]2[CH:3]=[C:2]([C:27]3[CH:32]=[CH:31][C:30]([CH:33]4[CH2:35][CH:34]4[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:29][CH:28]=3)[CH:7]=[CH:6][CH:5]=2)[CH:9]=1)=[O:20]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of amide from step 1 (1 eq), ethyl 2-(trans)-(4-bromophenyl)cyclopropanecarboxylate from EXAMPLE 1, step 1 (1 eq), Na2CO3 (3.5eq.; 2M in H2O), Pd(PPh3)4 (0.05 eq) in n-propanol (0.1M) was stirred at 80° C. for 3 h. The mixture was cooled to rt, quenched with brine and diluted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was triturated in ether/MeOH, isolated by filtration and washed with ether to afford the title compound as a solid.

Workup

temperatureThe mixture was cooled to rt
customquenched with brine
additiondiluted with EtOAc
washThe organic extracts were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was triturated in ether/MeOH
customisolated by filtration
washwashed with ether

Sources & evidence

ORD record: ord-953a890e4ea64df3ac1b48d81302a5ff
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342024B2

Reaction notes

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