1,8-Diazabicyclo(5.4.0)undec-7-ene → (S)-tert-butyl 2-(9H-pyrido[2,3-b]indol-6-yl)morpholine-4-carboxylate

HRID 710269Notes

Reaction equation

Cl[C:2]1[C:3]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.F[B-](F)(F)F.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C1CCN2C(=NCCC2)CC1>CC1C=CC=CC=1C.CC(N(C)C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:4]1[C:3]2[NH:8][C:9]3[C:14]([C:2]=2[CH:7]=[CH:6][CH:5]=1)=[CH:13][C:12]([C@@H:15]1[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]1)=[CH:11][CH:10]=3

Participants

Conditions

Temperature: 155 °C

Procedure

(S)-tert-Butyl 2-(4-(3-chloropyridin-2-ylamino)phenyl)morpholine-4-carboxylate (47 mg, 0.12 mmol), palladium(II)-acetate (2.7 mg, 0.012 mmol), tricyclohexylphosphine tetrafluoroborate (9 mg, 0.024 mmol) and DBU (37 mg, 0.24 mmol) were dissolved in a mixture of o-xylene (0.7 ml) and dimethylacetamide (0.7 ml). The mixture was degassed with argon for 5 min and heated at 155° C. for 16 h in a closed vial. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over MgSO4 and evaporated. Flash chromatography (2 g silica gel, 10 to 30% ethyl acetate in heptane) yielded a white solid (22 mg, 52%), MS (ISP): 354.3 ([M+H]+).

Workup

customThe mixture was degassed with argon for 5 min
temperatureAfter cooling
additionthe reaction mixture was poured into water
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over MgSO4
customevaporated

Sources & evidence

ORD record: ord-f911188b8e2a4391b3ea05a2392dd3d4
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181230B2

Reaction notes

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