ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Dimethylformamide → 6-(4-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine

HRID 331018
ノート
印刷プレビュー

反応式

HRID 331018 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:12])[CH:9]=[C:10](I)[C:3]=12.[CH3:13][N:14]1[CH2:19][CH2:18][O:17][C:16]2[CH:20]=[CH:21][C:22](B3OC(C)(C)C(C)(C)O3)=[CH:23][C:15]1=2.C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>C(#N)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:12])[CH:9]=[C:10]([C:22]3[CH:21]=[CH:20][C:16]4[O:17][CH2:18][CH2:19][N:14]([CH3:13])[C:15]=4[CH:23]=3)[C:3]=12
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 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 547587584-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazineHCID 710901484-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 710901456-(4-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine収率 40.8%

試薬・触媒・溶媒 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
55 °C

実験手順

To a suspension of 4-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine (D7) (300 mg, 0.890 mmol) and 4-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (353 mg, 1.283 mmol) in ACN (2.5 mL) was added 2M sodium carbonate aqueous solution (4.72 mL, 9.43 mmol). DMF (4 mL) and DCM (3 mL) were added to aid the solubility. Then, bis(triphenylphosphine)palladium(II)chloride (81 mg, 0.116 mmol) was added and the reaction was stirred at 55° C. for 30 mins. Volatiles were removed by evaporation before partitioning between DCM and water. The organic layer was separated, dried and concentrated. The crude material was purified on silica eluting with gradient of 0-40% ethyl acetate in cyclohexane to afford the title compound (130 mg). LCMS (A): m/z (M+H)+ 358/360, C17H16BrN3O requires 357/359 (acidic).

後処理

  1. customVolatiles were removed by evaporation
  2. custombefore partitioning between DCM and water
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customThe crude material was purified on silica eluting with gradient of 0-40% ethyl acetate in cyclohexane

出典と根拠

ORDレコード
ord-7b35ae86a6d149caa4e85bf45e555a4a
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08877742B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート