Sodium t-butoxide → HCID 178481730, compound

HRID 1854499Notes

Reaction equation

Cl[C:2]1[C:3]([C:11]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[N:12][NH:13][CH3:14])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.CC(C)([O-])C.[Na+]>CN1C(=O)CCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:15]1([C:11]2[C:3]3=[C:4]4[CH:10]=[CH:9][NH:8][C:5]4=[N:6][CH:7]=[C:2]3[N:13]([CH3:14])[N:12]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 5-chloro-4-(cyclohexyl(2-methylhydrazono)methyl)-1H-pyrrolo[2,3-b]pyridine (0.241 g, 0.829 mmol), sodium tert-butoxide (0.191 g, 1.99 mmol), palladium acetate (0.001 g, 0.0083 mmol) and (R)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-tert-butyl phosphine (0.0046 g, 0.0083 mmol), was heated in NMP (3 mL) at about 160° C. for about 15 min in a Biotage microwave. Additional palladium acetate (0.001 g, 0.0083 mmol) and (R)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-tert-butyl phosphine (0.0046 g, 0.0083 mmol) was added and the reaction mixture was heated at about 160° C. for about 30 min. The insoluble residue was removed by filtration through a Celite® pad and to the filtrate was purified by preparative RP-HPLC (Table 2, Method r) to provide 1-cyclohexyl-3-methyl-3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridine as a white solid (0.121 g, 58%): LC/MS (Table 2, Method d) Rt=2.29 min; m/z: 255 (M+H)+.

Workup

customThe insoluble residue was removed by filtration through a Celite® pad and to the filtrate
customwas purified by preparative RP-HPLC (Table 2, Method r)

Sources & evidence

ORD record: ord-8433077281c54695bb5a277d484ae80c
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962629B2

Reaction notes

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