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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Water → (S)-7-(3,3-dimethylbut-1-ynyl)-3-(2-fluoropyridin-4-yl)-2',6'-dihydrospiro[chromeno[2,3-b]pyridine-5,3'-[1,4]oxazin]-5'-amine

HRID 455678
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HRID 455678 반응식
Br[C:2]1[CH:3]=[C:4]2[C@@:15]3([N:20]=[C:19]([NH2:21])[CH2:18][O:17][CH2:16]3)[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:22]#[C:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:13]=3)[O:8][C:5]2=[N:6][CH:7]=1.[F:28][C:29]1[CH:34]=[C:33](B(O)O)[CH:32]=[CH:31][N:30]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CC1OCCC1.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[CH3:25][C:24]([CH3:27])([CH3:26])[C:23]#[C:22][C:12]1[CH:13]=[C:14]2[C@:15]3([N:20]=[C:19]([NH2:21])[CH2:18][O:17][CH2:16]3)[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:33]4[CH:32]=[CH:31][N:30]=[C:29]([F:28])[CH:34]=4)[CH:3]=3)[O:8][C:9]2=[CH:10][CH:11]=1
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7

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HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27833962-Fluoropyridine-4-boronic acidHCID 67387294(S)-3-bromo-7-(3,3-dimethylbut-1-ynyl)-2',6'-dihydrospiro[chromeno[2,3-b]pyridine-5,3'-[1,4]oxazin]-5'-amine

생성물 1

HCID 58465979(S)-7-(3,3-dimethylbut-1-ynyl)-3-(2-fluoropyridin-4-yl)-2',6'-dihydrospiro[chromeno[2,3-b]pyridine-5,3'-[1,4]oxazin]-5'-amine
수율 46.8%

시약·촉매·용매 2

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)촉매HCID 73012-Methyltetrahydrofuran용매

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온도
80 °C

실험 절차

A vial was charged with (S)-3-bromo-7-(3,3-dimethylbut-1-ynyl)-2′,6′-dihydrospiro[chromeno[2,3-b]pyridine-5,3′-[1,4]oxazin]-5′-amine (0.060 g, 0.141 mmol), 2-fluoropyridin-4-ylboronic acid (0.050 g, 0.352 mmol), potassium phosphate (0.299 g, 1.407 mmol) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (4.98 mg, 7.04 μmol) Dioxane (2 mL) and water (0.5 mL) were added, the vial was sealed under argon and heated to 80° C. for 1 hour. The reaction mixture was then diluted with 2-MeTHF, dried over MgSO4 and concentrated. Purification of the crude residue by column chromatography [0-100% (95:5 EtOAc/MeOH)/DCM] gave (S)-7-(3,3-dimethylbut-1-ynyl)-3-(2-fluoropyridin-4-yl)-2′,6′-dihydrospiro[chromeno[2,3-b]pyridine-5,3′-[1,4]oxazin]-5′-amine (0.029 g, 0.066 mmol, 46.6% yield) as a yellow solid. [M+H]+=443.0

후처리

  1. additionwere added
  2. customthe vial was sealed under argon
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customPurification of the crude residue by column chromatography [0-100% (95:5 EtOAc/MeOH)/DCM]

출처 및 근거

ORD 기록
ord-45b243c77f0940c99b680c6639bc4190
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08497264B2

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