Sodium Carbonate → 5-(2-bromo-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide

HRID 1473285

반응식

HRID 1473285 반응식
[CH3:1][O:2][C:3]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:4]=1[CH2:5][N:6]([C:29]1[S:33][N:32]=[CH:31][N:30]=1)[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2B2OC(C)(C)C(C)(C)O2)[CH:11]=1)(=[O:9])=[O:8].[Br:40][C:41]1[CH:46]=[C:45]([C:47]([F:50])([F:49])[F:48])[CH:44]=[CH:43][C:42]=1I.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.O.C(O)(C)(C)C.O1CCOCC1>[Br:40][C:41]1[CH:46]=[C:45]([C:47]([F:48])([F:49])[F:50])[CH:44]=[CH:43][C:42]=1[C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:17]=1[CH:18]=[CH:19][C:10]([S:7]([N:6]([CH2:5][C:4]1[CH:34]=[CH:35][C:36]([O:38][CH3:39])=[CH:37][C:3]=1[O:2][CH3:1])[C:29]1[S:33][N:32]=[CH:31][N:30]=1)(=[O:9])=[O:8])=[CH:11]2

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 162440892-Bromo-1-iodo-4-(trifluoromethyl)benzeneHCID 86687343N-(2,4-dimethoxybenzyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2 sulfonamide2회

생성물 1

HCID 866873425-(2-bromo-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide수율 69.8%

시약·촉매·용매 4

HCID 178418807HCID 178418807, 화합물촉매HCID 962Water용매2회HCID 6386tert-Butanol용매HCID 312751,4-Dioxane용매

반응 조건

온도
50 °C

실험 절차

A reaction vessel was charged with N-(2,4-dimethoxybenzyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2 sulfonamide (Intermediate E) (4 g, 7.05 mmol), 2-bromo-1-iodo-4-(trifluoromethyl)benzene (4.95 g, 14.10 mmol) and Pd(dppf)Cl2 DCM (1.151 g, 1.410 mmol). Dioxane (35.2 mL) and t-butanol (35.2 mL) were added to the reaction mixture followed by sodium carbonate in water (1.9 M) (11.13 mL, 21.15 mmol). The reaction vial was then swept with nitrogen and sealed with a screw cap. The resulting mixture was then heated to 50° C. and stirred for 4 hours. LC/MS indicated that the product was formed. The resulting mixture was transferred to a separatory funnel containing water and the aqueous layer was washed three times with DCM. The organic layers were combined, dried with MgSO4, filtered and concentrated to a dark oil which was purified by MPLC using 120 g silica gel column eluting with 0 to 70% EtOAc in heptane) to afford 5-(2-bromo-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)naphthalene-2-sulfonamide (3.27 g, 4.92 mmol) as a white solid. m/z (ESI) 685.8 [M+Na]+.

후처리

  1. customsealed with a screw
  2. customcap
  3. customwas formed
  4. customThe resulting mixture was transferred to a separatory funnel
  5. washthe aqueous layer was washed three times with DCM
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to a dark oil which
  9. customwas purified by MPLC
  10. washeluting with 0 to 70% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-1ea78afd9bd748e99a1c5f0a0d66a9eb
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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