Water → tert-Butyl 4-(2-(4-(4-amino-2-fluorophenoxy)pyridin-3-yl)ethynyl)cyclohex-3-enylcarbamate

HRID 2237223Notes

Reaction equation

[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]#[C:12][C:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:15][CH:14]=1.[NH4+].[Cl-].CN(C=O)C.O>[Fe].CCO>[NH2:31][C:29]1[CH:28]=[CH:27][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[C:11]#[C:12][C:13]2[CH2:18][CH2:17][CH:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:15][CH:14]=2)=[C:2]([F:1])[CH:30]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of tert-butyl 4-(2-(4-(2-fluoro-4-nitrophenoxy)pyridin-3-yl)ethynyl)cyclohex-3-enylcarbamate (110 mg, 0.24 mmol), iron powder, ˜325 mesh (150 mg, 2.7 mmol), NH4Cl (280 mg, 5.3 mmol), DMF (1 mL), H2O (1 mL) and EtOH (1 mL) was heated at 100° C. for 30 minutes. The mixture was filtered through a pad of Celite® using DMF to wash the filter cake and the filtrate made basic to pH 8 with saturated aq. NaHCO3 solution. The mixture was extracted twice with EtOAc and dried (MgSO4) and concentrated in vacuo to give the title compound (105 mg) which was used without any further purification. MS(ESI+): m/z 424.27 (M+H)+.

Workup

filtrationThe mixture was filtered through a pad of Celite®
washto wash the filter cake
extractionThe mixture was extracted twice with EtOAc
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2132349e7ff842bc8d1769391fc48120
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714138B2

Reaction notes

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