Dimethyl Sulfoxide → 3-[3-(1,1-Dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2-yl]-2,2-dimethylpropionaldehyde

HRID 2210559노트

반응식

HRID 2210559 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]([CH3:50])([S:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=3)[CH:22]=2)[N:17]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)[C:16]=1[CH2:44][C:45]([CH3:49])([CH3:48])[CH2:46][OH:47])[CH3:13].C(N(CC)CC)C>C(Cl)Cl>[CH3:13][C:12]([CH3:50])([S:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=3)[CH:22]=2)[N:17]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)[C:16]=1[CH2:44][C:45]([CH3:49])([CH3:48])[CH:46]=[O:47])[CH3:11]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 193790463-[3-(1,1-Dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2-yl]-2,2-dimethylpropanol

생성물 1

HCID 193790433-[3-(1,1-Dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2-yl]-2,2-dimethylpropionaldehyde수율 86.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of oxalyl chloride (461 mg, 3.6 mmol) in CH2Cl2 (10 mls) at -78° C. was added dimethylsulfoxide (600 mg, 7.68 mmol) dropwise and the resulting mixture was stirred for 5 mins. A solution of 3-[3-(1,1-dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2yl]-2,2-dimethylpropanol (1.81 g, 3.2 mmol) in CH2Cl2 (5 mls) was then added dropwise and the reaction was stirred for 20 mins at -78° C. Triethylamine (1,62 g, 16.0 mmol) was then added dropwise, the cooling bath was withdrawn and the reaction allowed to warm to r.t. It was then diluted with aqueous sat'd NaHCO3 (20 mls) and the layers were separated. The aqueous was extracted with CH2Cl2 (2×20 mls). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, ether:hexanes, 1:1) to afford 1.58 g (86%) of 3-[3-(1,1-dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2-yl]-2,2-dimethylpropionaldehyde as a lemon yellow solid.

후처리

  1. stirringthe reaction was stirred for 20 mins at -78° C
  2. customthe cooling bath was withdrawn
  3. additionIt was then diluted with aqueous sat'd NaHCO3 (20 mls)
  4. customthe layers were separated
  5. extractionThe aqueous was extracted with CH2Cl2 (2×20 mls)
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. customThe resulting residue was chromatographed (silica gel, ether:hexanes, 1:1)

출처 및 근거

ORD 기록
ord-7d7e3d7d869e4301969a7452469ed675
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05459150

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