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Sodium Carbonate → 5-(3-Benzyloxy-1-fluoro-7-vinylnaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 889262
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HRID 889262 반응식
[CH2:1]([O:8][C:9]1[C:10]([N:21]2[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:28])[CH2:22]2)=[C:11]([F:20])[C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14](Br)[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][C:30]1(C)C(C)(C)OB(C=C)O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[CH2:1]([O:8][C:9]1[C:10]([N:21]2[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:28])[CH2:22]2)=[C:11]([F:20])[C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14]([CH:29]=[CH2:30])[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 684322095-(3-(Benzyloxy)-7-bromo-1-fluoronaphthalen-2-yl)-1,2,5-thiadiazolidin-3-one 1,1-dioxide

생성물 1

HCID 684293215-(3-Benzyloxy-1-fluoro-7-vinylnaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane
용매

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온도
110 °C

실험 절차

To a microwave vial is added 5-(3-benzyloxy-7-bromo-1-fluoronaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (340 mg, 0.73 mmol) (intermediate from preparing Example 16), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.24 mL, 1.46 mmol), polystyrene tetrakis(triphenylphosphine)palladium(0) (0.1 mmole/g) (365 mg, 0.0365 mmol), Na2CO3 (2 M, 1.83 mL, 3.65 mmol) and DME (2.5 mL). The mixture is then heated in a microwave at 110° C. for 30 min. The resin is then filtered and the residue is purified quickly by Biotage reverse phase, eluting with 10-90% EtOH/water to give fractions containing the title compound: MS (M+H)+=413. The fractions are combined and used in the next step without concentration.

후처리

  1. filtrationThe resin is then filtered
  2. customthe residue is purified quickly by Biotage reverse phase
  3. washeluting with 10-90% EtOH/water
  4. customto give fractions

출처 및 근거

ORD 기록
ord-da2af255f5e443be8bab1732c66f07ce
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08252820B2

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