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Dichloromethane → 4'-(5-Aminopyridin-2-yl)-N-tert-butyl-3'-fluorobiphenyl-2-sulfonamide

HRID 1523944
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HRID 1523944 반응식
[C:1]([NH:5][S:6]([C:9]1[C:10]([C:15]2[CH:20]=[CH:19][C:18](B3OC(C)(C)C(C)(C)O3)=[C:17]([F:30])[CH:16]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:32]1[N:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>C(OCC)(=O)C.O.O1CCOCC1>[NH2:38][C:35]1[CH:34]=[CH:33][C:32]([C:18]2[CH:19]=[CH:20][C:15]([C:10]3[C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:8])=[O:7])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:16][C:17]=2[F:30])=[N:37][CH:36]=1
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참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 6428116-Bromopyridin-3-amineHCID 90313401N-(tert-butyl)-3'-fluoro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-sulfonamide

생성물 1

HCID 903139274'-(5-Aminopyridin-2-yl)-N-tert-butyl-3'-fluorobiphenyl-2-sulfonamide

시약·촉매·용매 3

HCID 962
Water
용매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

실험 절차

N-(tert-Butyl)-3′-fluoro-4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-2-sulfonamide (37 mg, 0.085 mmol) and 6-bromopyridin-3-amine (22 mg, 0.13 mmol) were added to a 5 mL sealable vial equipped with a stir bar. 1,4-Dioxane (0.2 mL) and 2 M Na2CO3 (0.2 mL) were added. Argon was bubbled through the solvent while it was rapidly stirred for 10 min then Pd(dppf)Cl2.CH2Cl2 (3 mg, 0.004 mmol) was added, and the mixture stirred for 15 hours at 80° Celsius under an argon atmosphere. The reaction was diluted with 2 mL of ethyl acetate and 2 mL of water and the aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organic extracts were then dried with Na2SO4 and concentrated to dryness. The crude product was purified by HPLC to give the title compound. MS (ESI): mass calcd. for C21H22FN3O2S, 399.14; m/z found, 400.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.66 (s, 1H), 8.25-8.16 (dd, J=8.0, 1.4, 1H), 7.83-7.76 (dd, J=8.8, 1.7, 1H), 7.77-7.68 (m, 1H), 7.66-7.58 (m, 1H), 7.58-7.48 (m, 2H), 7.46-7.39 (m, 2H), 7.37-7.30 (dd, J=7.4, 1.5, 1H), 4.31 (s, 1H), 1.09 (s, 9H).

후처리

  1. customequipped with a stir bar
  2. customArgon was bubbled through the solvent while it
  3. stirringthe mixture stirred for 15 hours at 80° Celsius under an argon atmosphere
  4. extractionthe aqueous layer was extracted with ethyl acetate (3×10 mL)
  5. dry with materialThe combined organic extracts were then dried with Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe crude product was purified by HPLC

출처 및 근거

ORD 기록
ord-b2c9bd5e1f0f4802875578a487a8c5d2
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09079866B2

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