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Dichloromethane → 2-Methyl-propane-2-sulfinic acid (3-{-4-[3,6-dioxo-8-phenyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,6-dihydro-3H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalen-7-yl]-phenyl}-oxetan-3-yl)-amide

HRID 1037326
ノート
印刷プレビュー

反応式

HRID 1037326 の反応式
I[C:2]1[C:3](=[O:30])[C:4]2[CH:5]=[CH:6][N:7]3[C:20](=[O:21])[N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[N:18]=[C:8]3[C:9]=2[O:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC1(C)C(C)(C)OB([C:39]2[CH:44]=[CH:43][C:42]([C:45]3([NH:49][S:50]([C:52]([CH3:55])([CH3:54])[CH3:53])=[O:51])[CH2:48][O:47][CH2:46]3)=[CH:41][CH:40]=2)O1.ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].COCCOC>[O:21]=[C:20]1[N:7]2[CH:6]=[CH:5][C:4]3[C:3](=[O:30])[C:2]([C:39]4[CH:40]=[CH:41][C:42]([C:45]5([NH:49][S:50]([C:52]([CH3:55])([CH3:54])[CH3:53])=[O:51])[CH2:48][O:47][CH2:46]5)=[CH:43][CH:44]=4)=[C:11]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[O:10][C:9]=3[C:8]2=[N:18][N:19]1[CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 670678002-Methyl-propane-2-sulfinic acid {3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-phenyl]-oxetan-3-yl}-amideHCID 866710397-Iodo-8-phenyl-2-(2-trimethylsilanyl-ethoxymethyl)-2H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalene-3,6-dione

生成物 1

HCID 86671050
2-Methyl-propane-2-sulfinic acid (3-{-4-[3,6-dioxo-8-phenyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,6-dihydro-3H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalen-7-yl]-phenyl}-oxetan-3-yl)-amide
収率 70%

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
125 °C

実験手順

A mixture of 7-iodo-8-phenyl-2-(2-trimethylsilanyl-ethoxymethyl)-2H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalene-3,6-dione (53.5 mg, 0.10 mmol), 2-methyl-propane-2-sulfinic acid {3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-phenyl]-oxetan-3-yl}-amide (57 mg, 0.15 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex with dichloromethane (4 mg, 0.005 mmol), sodium carbonate solution (2 M in water, 0.3 mL, 0.6 mmol) and DME (2 mL) was purged using nitrogen and heated in a microwave reactor at 125° C. for 1 h. The reaction mixture was allowed to cool to RT and was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc and the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 5 (% MeOH in EtOAc) to afford the title compound (46 mg, 70%) as a yellow gum. LCMS (Method H): RT=3.95 min, [M+H]+=661.

後処理

  1. customwas purged
  2. temperatureto cool to RT
  3. customwas partitioned between EtOAc and water
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washthe combined organic extracts were washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-30e183dde44a4fdba746da42c531f780
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546376B2

反応ノート

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