Sodium Carbonate → N-(2-chloro-5-(6-phthalazinyl)-3-pyridinyl)-4-fluorobenzenesulfonamide

HRID 1963783노트

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HRID 1963783 반응식
[Cl:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][N:3]=1.Br[C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[CH:35]=[N:34][N:33]=[CH:32]2.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[Cl:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)(=[O:10])=[O:11])=[CH:6][C:5]([C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[CH:35]=[N:34][N:33]=[CH:32]3)=[CH:4][N:3]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 6104366-BromophthalazineHCID 53363355n-[2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]-4-fluorobenzene-1-sulfonamide

생성물 1

HCID 44609856N-(2-chloro-5-(6-phthalazinyl)-3-pyridinyl)-4-fluorobenzenesulfonamide

시약·촉매·용매 3

HCID 53485975CID 53485975촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A suspension of N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (102 mg, 247 μmol), 6-bromophthalazine (43 mg, 206 μmol), dichloro[1,1′bis(diphenylphoshino)ferrocene]palladium(II)dichloromethane adduct (11 mg, 15 μmol), and Na2CO3 (65 mg, 617 μmol) in 1,4-dioxane (2 mL) and water (1 mL) was sparged with nitrogen for 5 minutes, then heated to 100° C. for 2 hours. The reaction was then partitioned between 9:1 CHCl3/IPA (30 mL) and 5% NaHCO3 (10 mL). The separated organic was dried over Na2SO4, concentrated onto dry silica, and then purified on silica eluting with 2→5% of MeOH/DCM. Product was isolated as light yellow solid. MS (ESI pos. ion) m/z calc'd for C19H12ClFN4O2S: 414.0; found 415.0. 1H NMR (400 MHz, DMSO-d6) δ 7.44 (t, J=8.8 Hz, 2 H) 7.80-7.87 (m, 2 H) 8.24 (d, J=2.1 Hz, 1 H) 8.32 (d, J=8.4 Hz, 1 H) 8.38 (dd, J=8.7, 2.0 Hz, 1 H) 8.54 (s, 1 H) 8.79 (d, J=2.1 Hz, 1 H) 9.76 (s, 2 H) 10.60 (s, 1 H).

후처리

  1. customwas sparged with nitrogen for 5 minutes
  2. customThe reaction was then partitioned between 9:1 CHCl3/IPA (30 mL) and 5% NaHCO3 (10 mL)
  3. dry with materialThe separated organic was dried over Na2SO4
  4. concentrationconcentrated onto dry silica
  5. custompurified on silica eluting with 2→5% of MeOH/DCM
  6. customProduct was isolated as light yellow solid

출처 및 근거

ORD 기록
ord-a8b0ae99e7614b24bea78adece50f985
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415376B2

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