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Pivalic acid → 9-(Oxazol-5-yl)-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

HRID 926318
ノート
印刷プレビュー

反応式

HRID 926318 の反応式
I[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]1[C:16](=[O:17])[CH2:15][NH:14][C:13](=[O:18])[CH:12]=[C:7]12.[O:19]1[CH:23]=[CH:22][N:21]=[CH:20]1.C(P(C(C)(C)C)C1C(C)=C(C)C(C)=C(C)C=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.C([O-])([O-])=O.[K+].[K+].C(O)(=O)C(C)(C)C>CC(N(C)C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:19]1[C:23]([C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH2:4][CH2:5][N:6]2[C:16](=[O:17])[CH2:15][NH:14][C:13](=[O:18])[CH:12]=[C:7]23)=[CH:22][N:21]=[CH:20]1
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

8

反応物 5

HCID 6417Pivalic acidHCID 9255OxazoleHCID 11430Potassium CarbonateHCID 11953610Di-tert-butyl[3,4,5,6-tetramethyl-2',4',6'-tris(propan-2-yl)-[1,1'-biphenyl]-2-yl]phosphaneHCID 867113799-Iodo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

生成物 1

HCID 86711389
9-(Oxazol-5-yl)-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione
収率 32.3%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
120 °C

実験手順

112-1. A mixture of 9-iodo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione (520 mg, 1.47 mmol), oxazole (0.24 mL, 3.67 mmol), Pd(OAc)2 (49 mg, 0.22 mmol), di-tert-butyl(2′,4′,6′-triisopropyl-3,4,5,6-tetramethyl-[1,1′-biphenyl]-2-yl)phosphine (141 mg, 0.29 mmol), K2CO3 (609 mg, 4.40 mmol) and pivalic acid (68 μL, 0.59 mmol) in DMA (4 mL) was heated to 120° C. for 1 h in a microwave reactor. The mixture was then filtered and the filtrate was concentrated in vacuo. Purification of the obtained residue by flash chromatography (SiO2, AcOEt/MeOH 99:1 to 90:10) afforded the title compound (140 mg) as a beige powder. UPLC-MS: MS 296.1 (M+H+); UPLC rt 0.60 min.

後処理

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customPurification of the obtained residue by flash chromatography (SiO2, AcOEt/MeOH 99:1 to 90:10)

出典と根拠

ORDレコード
ord-4141d46575e84ec98719fdd0bbe61467
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09284331B2

反応ノート

読み込み中…

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