P-Anisidine → HCID 46843594, compound

HRID 533761Notes

Reaction equation

C(OC([N:8]1[CH2:16][CH2:15][C:14]2[NH:13][C:12]3[N:17]=[CH:18][CH:19]=[C:20](Cl)[C:11]=3[C:10]=2[CH2:9]1)=O)(C)(C)C.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[OH-].[K+]>C(O)(CC)(C)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:20]2[C:11]3[C:10]4[CH2:9][NH:8][CH2:16][CH2:15][C:14]=4[NH:13][C:12]=3[N:17]=[CH:18][CH:19]=2)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 95 °C

Procedure

4-Chloro-5,7,8,9-tetrahydro-dipyrido[2,3-b;3′,4′-d]pyrrole-6-carboxylic acid tert-butyl ester (100 mg, 0.32 mmol), p-anisidine (80 mg, 0.65 mmol), Pd(OAc)2 (3 mg, 0.01 mmol), X-Phos (12 mg, 0.03 mmol), and KOH (55 mg, 0.97 mmol) were suspended in tert-amyl alcohol (2 mL), and stirred overnight at 95° C. The crude product was purified directly via prep-LC-MS to provide 47 (3 mg, 3% yield) as a tan solid. LC-MS (M+H=295, obsd.=295).

Workup

customThe crude product was purified directly via prep-LC-MS

Sources & evidence

ORD record: ord-bff2061de4fd404dbe2ddfc13d263044
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853391B2

Reaction notes

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