1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 4-[5-(4-Methanesulfonyl-piperazin-1-yl)-2-methyl-2,3-dihydro-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1184776ノート

反応式

HRID 1184776 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2([CH3:24])[O:23][C:17]3=[CH:18][N:19]=[C:20](Cl)[CH:21]=[C:16]3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:26][S:27]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)(=[O:29])=[O:28].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2([CH3:24])[O:23][C:17]3=[CH:18][N:19]=[C:20]([N:33]4[CH2:34][CH2:35][N:30]([S:27]([CH3:26])(=[O:29])=[O:28])[CH2:31][CH2:32]4)[CH:21]=[C:16]3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 162656121-Methanesulfonylpiperazine hydrochlorideHCID 23665647Potassium tert-butoxideHCID 866749014-(5-Chloro-2-methyl-2,3-dihydrofuro[2,3-c]pyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 679902714-[5-(4-Methanesulfonyl-piperazin-1-yl)-2-methyl-2,3-dihydro-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
105 °C

実験手順

4-(5-Chloro-2-methyl-2,3-dihydro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (100 mg) is added to a mixture of 1-(methylsulfonyl)piperazine hydrochloride (70 mg), Pd2(dba)3 (65 mg), Xantphos (123 mg), and potassium tert-butylate (75 mg) in toluene (4 mL) under an argon atmosphere. The reaction mixture is stirred in an oil bath at 105° C. over night. After cooling to room temperature water is added and the mixture is extracted with ethyl acetate. The combined extracts are concentrated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:50→0:100) to give the title compound. LC (method 1): tR=1.03 min; Mass spectrum (ESI+): m/z=481 [M+H]+.

後処理

  1. additionis added
  2. extractionthe mixture is extracted with ethyl acetate
  3. concentrationThe combined extracts are concentrated in vacuo
  4. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:50→0:100)

出典と根拠

ORDレコード
ord-3b0a3207384e4f828e02748b94c924cb
出典データセット
uspto-grants-2014_03
特許番号
US08669271B2

反応ノート

読み込み中…