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

HRID 1502081ノート

反応式

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]

参加物

反応条件

温度: 100 °C

実験手順

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.

後処理

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)

出典と根拠

ORDレコード: ord-19c7f2cb4f414f2096af8bc3b95607f2
出典データセット: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09206199B2

反応ノート

読み込み中…

反応式

参加物

反応物 5

生成物 1

試薬・触媒・溶媒 2

反応条件

実験手順

後処理

出典と根拠

反応ノート