6-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole → HCID 18180310, 화합물

HRID 1359069노트

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HRID 1359069 반응식
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:27][C:17]3=[C:18]4[C:23](=[CH:24][CH:25]=[C:16]3[O:15][CH2:14]2)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]4)(=O)=O)=CC=1.[Cl:28][C:29]1[CH:37]=[C:36]2[C:32]([C:33]([C:38]3[CH2:39][CH2:40]NCC=3)=[CH:34][NH:35]2)=[CH:31][CH:30]=1>CS(C)=O>[Cl:28][C:29]1[CH:37]=[C:36]2[C:32]([C:33]([CH2:38][CH:39]3[CH2:40][CH2:23][N:22]([CH2:12][CH:13]4[O:27][C:17]5=[C:18]6[C:23](=[CH:24][CH:25]=[C:16]5[O:15][CH2:14]4)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]6)[CH2:21][CH2:20]3)=[CH:34][NH:35]2)=[CH:31][CH:30]=1

참가 물질

4

반응물 2

HCID 100598546-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 11280604(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl 4-methylbenzenesulfonate

생성물 1

HCID 18180310HCID 18180310, 화합물

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
75 °C

실험 절차

(2R)-8-Methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl 4-methylbenzenesulfonate (0.55 g, 1.4 mmole) and 6-chloro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.80 g, 3.4 mmole) were combined in 10 mL of DMSO. The mixture was heated at 70-80° C. under nitrogen for 6 hours. After cooling to room temperature, the mixture was partitioned between 400 mL each of ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was removed, washed with 400 mL portions of water and saturated brine, dried over sodium sulfate, filtered and concentrated to dryness under vacuum. The residue was column chromatographed on silica gel using 0-2% methanol/chloroform. The product fractions were concentrated in vacuum to give 0.27 g of the (S)-enantiomer of the title compound as an amorphous orange solid, which retains 0.35 equivalents of chloroform.

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between 400 mL each of ethyl acetate and saturated aqueous sodium bicarbonate
  3. customThe organic phase was removed
  4. washwashed with 400 mL portions of water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under vacuum
  8. customchromatographed on silica gel using 0-2% methanol/chloroform
  9. concentrationThe product fractions were concentrated in vacuum

출처 및 근거

ORD 기록
ord-7b133e966bc24b7a914e6ecf9170b7ac
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599915B2

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