Dimethyl Sulfoxide → Methyl 3-cyclohexyl-2-(2-formyl-4-methoxyphenyl)-1-prop-2-yn-1-yl-1H-indole-6-carboxylate

HRID 1518263ノート

反応式

HRID 1518263 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH:11]1([C:17]2[C:25]3[C:20](=[CH:21][C:22]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:24]=3)[N:19]([CH2:30][C:31]#[CH:32])[C:18]=2[C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=2[CH2:41][OH:42])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.CCN(CC)CC>C(Cl)Cl>[CH:11]1([C:17]2[C:25]3[C:20](=[CH:21][C:22]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:24]=3)[N:19]([CH2:30][C:31]#[CH:32])[C:18]=2[C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=2[CH:41]=[O:42])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86637863Methyl 3-cyclohexyl-2-[2-(hydroxymethyl)-4-methoxyphenyl]-1-prop-2-yn-1-yl-1H-indole-6-carboxylate

生成物 1

HCID 86637864Methyl 3-cyclohexyl-2-(2-formyl-4-methoxyphenyl)-1-prop-2-yn-1-yl-1H-indole-6-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

Oxalyl chloride (2.5 eq., 2M solution in DCM) was added at −70° C. under nitrogen atmosphere over a solution of DMSO (5 eq.) in anhydrous DCM and the mixture was stirred for 30 min; a solution of methyl 3-cyclohexyl-2-[2-(hydroxymethyl)-4-methoxyphenyl]-1-prop-2-yn-1-yl-1H-indole-6-carboxylate in DCM was then added and stirring was continued at the same temperature for 30 min. before NEt3 (8 eq.) was added. After stirring at 0° C. for 20 min. the mixture was diluted with DCM, washed with water, 1N HCl, saturated aq. NaHCO3 solution and brine. The organic phase was dried over Na2SO4 and evaporated in vacuo. The obtained yellow solid was used in the next step without purification. MS (ES+): 430.5 (M+H+).

後処理

  1. stirringstirring
  2. additionwas added
  3. stirringAfter stirring at 0° C. for 20 min. the mixture
  4. washwashed with water, 1N HCl, saturated aq. NaHCO3 solution and brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated in vacuo
  7. customThe obtained yellow solid was used in the next step without purification

出典と根拠

ORDレコード
ord-90833dcb6db043a785b14910492a3482
出典データセット
uspto-grants-2012_07
特許番号
US08232390B2

反応ノート

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