Diisopropylethylamine → tert-butyl 3-(1-(2-(dimethylamino)ethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylthio)azetidine-1-carboxylate

HRID 241637ノート

反応式

HRID 241637 の反応式
Br[C:2]1[CH:20]=[CH:19][C:5]2[N:6]([CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[C:7]([CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[N:8][C:4]=2[CH:3]=1.[SH:21][CH:22]1[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:23]1.C(N(CC)C(C)C)(C)C>O1CCOCC1.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].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>[CH3:17][N:16]([CH3:18])[CH2:15][CH2:14][N:6]1[C:5]2[CH:19]=[CH:20][C:2]([S:21][CH:22]3[CH2:23][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25]3)=[CH:3][C:4]=2[N:8]=[C:7]1[CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11]

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 58513580tert-Butyl 3-sulfanylazetidine-1-carboxylateHCID 585135832-(5-bromo-2-neopentyl-1H-benzo[d]imidazol-1-yl)-N,N-dimethylethanamine

生成物 1

HCID 58513595tert-butyl 3-(1-(2-(dimethylamino)ethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylthio)azetidine-1-carboxylate収率 99%

試薬・触媒・溶媒 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
160 °C

実験手順

A mixture of 2-(5-bromo-2-neopentyl-1H-benzo[d]imidazol-1-yl)-N,N-dimethylethanamine (STEP A, 338 mg, 1.00 mmol), tert-butyl 3-mercaptoazetidine-1-carboxylate (STEP D, 246 mg, 1.30 mmol), Xantphos (28.9 mg, 0.0500 mmol), tris(dibenzylideneacetone)dipalladium (22.3 mg, 0.0250 mmol) and N,N-diisopropylethylamine (262 microL, 1.50 mmol) in 1,4-dioxane (4 mL) was stirred at 160° C. for 1 h under microwave. The mixture was concentrated in vacuo and the residue was purified by amine gel column chromatography (hexane-ethyl acetate, gradient) to give the title compound (442 mg, 99%) as a yellow oil.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by amine gel column chromatography (hexane-ethyl acetate, gradient)

出典と根拠

ORDレコード
ord-ec0680c307d54a0eaca4c77edb76948b
出典データセット
uspto-grants-2014_02
特許番号
US08653063B2

反応ノート

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