Ethyl Acetate → (5-fluoroadamantan-2-yl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-2(1H)-one

HRID 1360204Notes

Reaction equation

HRID 1360204 reaction equation
O[C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[N:12]3[C:16]4=[C:17]5[CH:23]=[CH:22][NH:21][C:18]5=[N:19][CH:20]=[C:15]4[NH:14][C:13]3=[O:24])[CH2:3]1)[CH2:9]2.C(S(F)(F)([F:31])(CC)N)C.C(=O)([O-])O.[Na+].C(OCC)(=O)C>ClCCl>[F:31][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[N:12]3[C:16]4=[C:17]5[CH:23]=[CH:22][NH:21][C:18]5=[N:19][CH:20]=[C:15]4[NH:14][C:13]3=[O:24])[CH2:3]1)[CH2:9]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 53748433Diethyl aminosulfur trifluorideHCID 57928254(5-Hydroxyadamantan-2-yl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-2(1H)-one

Product 1

HCID 57928284(5-fluoroadamantan-2-yl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5-Hydroxyadamantan-2-yl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-2(1H)-one (92 mg) was suspended in dichloromethane, and diethyl aminosulfur trifluoride (DAST) was added. The mixture was stirred at ambient temperature for 1 hour. The saturated aqueous sodium hydrogencarbonate and ethyl acetate were added. The obtained solid was collected by filtration and washed with diisopropyl ethylether to obtain (5-fluoroadamantan-2-yl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-2(1H)-one (34 mg).

Workup

  1. filtrationThe obtained solid was collected by filtration
  2. washwashed with diisopropyl ethylether

Sources & evidence

ORD record
ord-af50b2d42ac44520905041d2d1fae695
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

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