Potassium Carbonate → (3R,9aS)-tert-butyl 3-(3-cyano-2-cyclopropyl-4-fluorophenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

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Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([F:10])[CH:5]=[CH:4][C:3]=1[C@H:11]1[O:16][CH2:15][C@@H:14]2[CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20][N:13]2[CH2:12]1.[CH:28]1([B-](F)(F)F)[CH2:30][CH2:29]1.[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C(=O)([O-])[O-].[K+].[K+].COC1CCCC1>CC([O-])=O.CC([O-])=O.[Pd+2].O>[C:8]([C:7]1[C:2]([CH:28]2[CH2:30][CH2:29]2)=[C:3]([C@H:11]2[O:16][CH2:15][C@@H:14]3[CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20][N:13]3[CH2:12]2)[CH:4]=[CH:5][C:6]=1[F:10])#[N:9]

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온도: 100 °C

실험 절차

To a microwave vial was charged with (3R,9aS)-tert-butyl 3-(2-chloro-3-cyano-4-fluorophenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate (30 mg, 0.076 mmol), potassium cyclopropyltrifluoroborate (16.8 mg, 0.114 mmol), Pd(OAc)2 (1.7 mg, 7.58 μmol), X-Phos (7.2 mg, 0.015 mmol), and potassium carbonate (31.4 mg, 0.227 mmol). CPME (0.4 mL) and Water (40 μL) were added, and the reaction mixture was degassed with N2 and heated at 100° C. for 24 h. The reaction mixture was filtered to give the crude product, which was purified by prep-TLC (1000 μm, 5% MeOH/DCM) to give the title compound: LC/MS: [(M+1-56)]+=346.3.

후처리

customthe reaction mixture was degassed with N2
filtrationThe reaction mixture was filtered
customto give the crude product, which
customwas purified by prep-TLC (1000 μm, 5% MeOH/DCM)

출처 및 근거

ORD 기록: ord-19c7f2cb4f414f2096af8bc3b95607f2
출처 데이터셋: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09206199B2

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