Potassium Carbonate → N-(difluoromethyl)-N-{2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide

HRID 1960512ノート

反応式

HRID 1960512 の反応式
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH:8]2[S:12][C:11]([C:13]3[NH:14][C:15]4[C:20]([CH:21]=3)=[CH:19][CH:18]=[CH:17][C:16]=4[NH:22][S:23]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)(=[O:25])=[O:24])=[N:10][CH2:9]2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[F:37][CH:38]([F:40])I>CN(C)C=O.C(OCC)(=O)C>[F:37][CH:38]([F:40])[N:22]([C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[NH:14][C:13]([C:11]1[S:12][CH:8]([CH2:7][N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)[CH2:9][N:10]=1)=[CH:21]2)[S:23]([C:26]1[S:27][CH:28]=[CH:29][CH:30]=1)(=[O:24])=[O:25]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 2775155Difluoro(iodo)methaneHCID 59135769N-{2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide

生成物 1

HCID 24899516N-(difluoromethyl)-N-{2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide収率 27.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of N-{2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide (200 mg) in N,N-dimethylformamide (3 mL) were added potassium carbonate (90.0 mg) and difluoroiodomethane (77.0 mg), and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried (MgSO4), and concentrated. The residue was subjected to basic silica gel column chromatography to give the title compound (60 mg, yield 27%) as white crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS:513(MH+). melting point 185-186° C.

後処理

  1. washwashed with water and saturated brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-b2ca271f34db42afb2cf13e632fd6f5e
出典データセット
uspto-grants-2013_04
特許番号
US08410087B2

反応ノート

読み込み中…