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Nitrogen → (3R,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2,5-dimethylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

HRID 1502078
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HRID 1502078 반응식
[C:1]([C:3]1[C:4]([CH3:28])=[C:5]([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:6]=[C:7](I)[C:8]=1[F:9])#[N:2].[C:29]([O-])([O-])=O.[Cs+].[Cs+].N#N.C1(C)C=CC=CC=1.O>O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([C:3]1[C:4]([CH3:28])=[C:5]([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:6]=[C:7]([CH3:29])[C:8]=1[F:9])#[N:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 947NitrogenHCID 10796Cesium carbonateHCID 22272177Toluene waterHCID 117690096(3R,9aS)-tert-butyl 3-(3-cyano-4-fluoro-5-iodo-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

생성물 1

HCID 89633504(3R,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2,5-dimethylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

시약·촉매·용매

2
HCID 167845palladium(II) acetate촉매HCID 962Water용매

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온도
80 °C

실험 절차

To a vial was charged with (3R,9aS)-tert-butyl 3-(3-cyano-4-fluoro-5-iodo-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate (50 mg, 0.10 mmol), MeBF3K (24 mg, 0.20 mmol), Pd(OAc)2 (2.2 mg, 0.01 mmol), Ru-Phos (9.3 mg, 0.02 mmol), and Cs2CO3 (97 mg, 0.3 mmol). The vial was sealed, vacuumed, and refilled with N2. PhMe/H2O (0.5/0.05 mL) was added, and the reaction mixture was heated at 80° C. overnight. The reaction mixture was diluted with water, extracted with EtOAc, washed with brined and dried. The crude product was purified with prep-TLC (5% MeOH/DCM) to give title compound: LC/MS: [(M+1-56)]+=334.3.

후처리

  1. customThe vial was sealed
  2. extractionextracted with EtOAc
  3. washwashed with brined and
  4. customdried
  5. customThe crude product was purified with prep-TLC (5% MeOH/DCM)

출처 및 근거

ORD 기록
ord-cef9a04366e34722964b14c1937f6ba8
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09206199B2

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