Water → 1-(2-Chlorophenyl)-3-methyl-5-piperidin-1-yl-2-[4-(4,4,4-trifluorobutoxy)phenyl]-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine-4-one

HRID 254344

反応式

HRID 254344 の反応式
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:22]2[CH2:21][CH2:20][N:19]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[C:18](=[O:29])[C:17]=2[C:16]([CH3:30])=[C:15]1[C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1.I[CH2:39][CH2:40][CH2:41][C:42]([F:45])([F:44])[F:43].O>CN(C=O)C>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:22]2[CH2:21][CH2:20][N:19]([N:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)[C:18](=[O:29])[C:17]=2[C:16]([CH3:30])=[C:15]1[C:31]1[CH:32]=[CH:33][C:34]([O:37][CH2:39][CH2:40][CH2:41][C:42]([F:45])([F:44])[F:43])=[CH:35][CH:36]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium Carbonate2 回HCID 27751891,1,1-Trifluoro-4-iodobutane2 回HCID 166661641-(2-Chlorophenyl)-2-(4-hydroxyphenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine-4-one

生成物 1

HCID 166660071-(2-Chlorophenyl)-3-methyl-5-piperidin-1-yl-2-[4-(4,4,4-trifluorobutoxy)phenyl]-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine-4-one収率 40%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Potassium carbonate (0.19 g, 1.38 mmol) was added to a solution of 1-(2-chlorophenyl)-2-(4-hydroxyphenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine-4-one, from Ex. 1, Step 8 (0.50 g, 1.15 mmol) in DMF (30 ml) followed by 1-iodo-4,4,4-trifluorobutane (328 mg, 1.38 mmol). The reaction mixture was heated at 80° C. overnight. TLC showed very little conversion to starting material; 656 mg (2 eqv.) 1-iodo-4,4,4-trifluorobutane and 380 mg (2 eqv.) K2CO3 were added and heating continued for one hour. After cooling to rt, water was added and the product extracted with EtOAc (×3). The combined organic extracts were washed with brine (×2), dried (Na2SO4), filtered and concentrated. Flash chromatography (heptane:EtOAc gradient) afforded 250 mg (40%) of the title compound as a colorless solid.

後処理

  1. temperatureheating
  2. temperatureAfter cooling to rt
  3. extractionthe product extracted with EtOAc (×3)
  4. washThe combined organic extracts were washed with brine (×2)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-c2c1fa11c5e5454bac9bbb5b34986c39
出典データセット
uspto-grants-2011_01
特許番号
US07875626B2

関連ノート

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