Potassium Carbonate → HCID 86602862, compound

HRID 508520Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.C([O-])([O-])=O.[K+].[K+].[CH2:15]([NH:17][C:18](=[O:20])[O-:19])[CH3:16].[CH3:21][O:22][C:23]1[C:24](Br)=[CH:25][C:26]2[CH:27]([CH3:35])[CH:28]3[CH2:32][NH:31][CH2:30][CH:29]3[C:33]=2[CH:34]=1>O1CCOCC1.O.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>[CH2:15]([NH:17][C:18](=[O:19])[O-:20])[CH3:16].[CH3:21][O:22][C:23]1[C:24]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[CH:25][C:26]2[CH:27]([CH3:35])[CH:28]3[CH2:32][NH:31][CH2:30][CH:29]3[C:33]=2[CH:34]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Thiophene-2-boronic acid (44 mg, 0.34 mmol), Pd(PPh3)4 (19 mg, 0.02 mmol), K2CO3 (71 mg, 0.51 mmol), and H2O (0.17 mL) were added to a solution of N-ethylcarbamate-5-methoxy-6-bromo-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 30, Step A) (60 mg, 0.17 mmol) in dioxane (3 mL) and stirred overnight at 100° C. The reaction mixture was diluted with EtOAC and H2O, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via a silica plug eluting with Hexanes/EtOAc (2/1, v/v). MS calculated for C20H25NO3S+H: 358, observed: 358.

Workup

filtrationfiltered through an Extrelut column
washThe column was washed with EtOAc
concentrationthe filtrate was concentrated
customThe crude product was purified via a silica plug
washeluting with Hexanes/EtOAc (2/1

Sources & evidence

ORD record: ord-a597c2cae42f4d8a8973f4d05ad72fb6
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096520B2

Reaction notes

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