Sodium Carbonate → N-Benzyl-N-[5-[3-(methylsulfonyl)-4-(hydroxymethyl)phenyl]thiophene-2-ylmethyl]-2-(trifluoromethyl)benzenesulfonamide

HRID 1665069ノート

反応式

HRID 1665069 の反応式
[CH2:1]([N:8]([CH2:22][C:23]1[S:24][C:25](Br)=[CH:26][CH:27]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][S:30]([C:33]1[CH:38]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH:36]=[CH:35][C:34]=1[CH2:48][OH:49])(=[O:32])=[O:31].[F-].[Cs+].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].ClCCl.COCCOC>[CH2:1]([N:8]([CH2:22][C:23]1[S:24][C:25]([C:37]2[CH:36]=[CH:35][C:34]([CH2:48][OH:49])=[C:33]([S:30]([CH3:29])(=[O:32])=[O:31])[CH:38]=2)=[CH:26][CH:27]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 25953Cesium fluorideHCID 59251458(2-(Methylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanolHCID 67439229N-benzyl-N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamide

生成物 1

HCID 25210583N-Benzyl-N-[5-[3-(methylsulfonyl)-4-(hydroxymethyl)phenyl]thiophene-2-ylmethyl]-2-(trifluoromethyl)benzenesulfonamide収率 39%

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

A suspension of N-benzyl-N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamide (example 1, step 2, 170 mg), [2-methanesulfonyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanol (CAS [918328-16-2], 90 mg), cesium fluoride (88 mg) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium dichloromethane adduct (12 mg) in a 1 M aqueous sodium carbonate solution (0.72 mL) and 1,2-dimethoxyethane (1.5 mL) was heated to 80° C. for 36 h. After cooling to r.t., the mixture was filtered. The filtrate was diluted with ethyl acetate and washed with water. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure. The product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:0 to 0:1) to give N-benzyl-N-[5-(4-hydroxymethyl-3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-2-trifluoromethyl-benzenesulfonamide (67 mg) as an off-white solid. MS: 612.6 ([M+NH4]+)

後処理

  1. temperatureAfter cooling to r.t.
  2. filtrationthe mixture was filtered
  3. additionThe filtrate was diluted with ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:0 to 0:1)

出典と根拠

ORDレコード
ord-0acb9b7649b54d45a106638a39c171ee
出典データセット
uspto-grants-2011_10
特許番号
US08039493B2

反応ノート

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