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

HRID 1473285

反応式

HRID 1473285 の反応式
[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

参加物

8

反応物 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 sulfonamide2 回

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418807HCID 178418807、化合物触媒HCID 962Water溶媒2 回HCID 6386tert-Butanol溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-1ea78afd9bd748e99a1c5f0a0d66a9eb
出典データセット
uspto-grants-2015_04
特許番号
US09012443B2

関連ノート

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