Triphenylphosphine → HCID 57812426, compound

HRID 911981Notes

Reaction equation

[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([Cl:10])[C:3]=1[CH:11]([OH:13])[CH3:12].[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([N:27]2[CH:31]=[C:30]([C:32]3[C:36]4[CH:37]=[N:38][C:39]([N+:42]([O-:44])=[O:43])=[C:40](O)[C:35]=4[O:34][CH:33]=3)[CH:29]=[N:28]2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([Cl:10])[C:3]=1[CH:11]([O:13][C:40]1[C:35]2[O:34][CH:33]=[C:32]([C:30]3[CH:29]=[N:28][N:27]([CH:24]4[CH2:23][CH2:22][N:21]([C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:20])[CH2:26][CH2:25]4)[CH:31]=3)[C:36]=2[CH:37]=[N:38][C:39]=1[N+:42]([O-:44])=[O:43])[CH3:12]

Participants

Conditions

Temperature: 40 °C

Procedure

1-(2,6-Dichloro-3,5-difluorophenyl)ethanol (133 mg, 0.586 mmol), 4-[4-(7-Hydroxy-6-nitrofuro[3,2-c]pyridin-3-yl)-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (250 mg, 0.52 mmol), PPh3 (410 mg, 1.60 mmol) and THF (20 mL) was added to a dry round bottom flask. Diisopropyl azodicarboxylate (320 mg, 1.60 mmol) was added and the reaction mixture was heated at 40° C. More DIAD (320 mg, 1.60 mmol) was then added and the reaction mixture was heated at 40° C. for 2 h. Purification by flash column chromatography using 10%→40% EtOAc in hexanes afforded the title compound as a yellow solid. MS (ES+): m/z 581.88/583.80 (100/80) [MH+−isobutene]. HPLC: tR=4.29 min (ZQ3, polar—5 min).

Workup

temperaturethe reaction mixture was heated at 40° C. for 2 h
customPurification by flash column chromatography

Sources & evidence

ORD record: ord-f262bc85d3714a4697c581bd6281b6e5
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022206B2

Reaction notes

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