Tetrahydrofuran → HCID 118248889, compound

HRID 1775440Notes

Reaction equation

HRID 1775440 reaction equation
Br[C:2]1[CH:3]=[C:4]2[O:27][CH2:26][CH2:25][C:5]2=[C:6]2[C:10]=1[NH:9][C:8]([C:11](=[O:14])[NH:12][CH3:13])=[C:7]2[CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].C(N(CC)CC)C.O1CCCC1>[Pd].C(O)C>[CH3:13][NH:12][C:11]([C:8]1[NH:9][C:10]2[C:6]([C:7]=1[CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[C:5]1[CH2:25][CH2:26][O:27][C:4]1=[CH:3][CH:2]=2)=[O:14]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 118074740HCID 118074740, compound

Product 1

HCID 118248889HCID 118248889, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of tert-butyl {2-[5-bromo-7-(methylcarbamoyl)-1,6-dihydro-2H-furo[3,2-e]indol-8-yl]ethyl}carbamate (569 mg), triethylamine (0.724 mL), tetrahydrofuran (10.0 mL), and ethanol (30.0 mL) was added 10% palladium on carbon (50% water included, 284 mg) under an argon gas flow, followed by stirring at room temperature overnight under a hydrogen atmosphere (3.2 kgf/cm2). The catalyst was separated by filtration and the filtrate was concentrated under reduced pressure to obtain tert-butyl {2-[7-(methylcarbamoyl)-1,6-dihydro-2H-furo[3,2-e]indol-8-yl]ethyl}carbamate (434 mg) as a pale yellow solid.

Workup

  1. customThe catalyst was separated by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-30a97959a4704d65aad57404863cd81c
Source dataset
uspto-grants-2016_02
Patent number
US09260445B2

Reaction notes

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