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

HRID 2210559ノート

反応式

HRID 2210559 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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was stirred for 20 mins at -78° C. Triethylamine (1,62 g, 16.0 mmol) was then added dropwise, the cooling bath was withdrawn and the reaction allowed to warm to r.t. It was then diluted with aqueous sat'd NaHCO3 (20 mls) and the layers were separated.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.

後処理

  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 customthe cooling bath was withdrawn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)

出典と根拠

ORDレコード
ord-7d7e3d7d869e4301969a7452469ed675
出典データセット
uspto-grants-1995_10
特許番号
US05459150

反応ノート

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