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

Potassium Carbonate → tert-butyl 6-(6-(methoxycarbonyl)-5-(3-phenoxypropoxy)pyridin-2-yl)-2H-benzo[b][1,4]oxazine-4(3H)-carboxylate

HRID 1641112
ノート
印刷プレビュー

反応式

HRID 1641112 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:25]=[CH:24][C:12]3[O:13][CH2:14][CH2:15][N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:11]=3[CH:10]=2)O1.Br[C:28]1[N:33]=[C:32]([C:34]([O:36][CH3:37])=[O:35])[C:31]([O:38][CH2:39][CH2:40][CH2:41][O:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:30][CH:29]=1.C([O-])([O-])=O.[K+].[K+].O1CCO[CH2:57][CH2:56]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:37][O:36][C:34]([C:32]1[N:33]=[C:28]([C:9]2[CH:25]=[CH:24][C:12]3[O:13][CH2:14][CH2:15][N:16]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C:11]=3[CH:10]=2)[CH:29]=[CH:30][C:31]=1[O:38][CH2:39][CH2:40][CH2:41][O:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:35].[CH3:37][O:36][C:34]([C:32]1[N:33]=[C:28]([C:9]2[CH:25]=[CH:24][C:12]3[O:13][CH2:14][CH2:15][N:16]([C:17]([O:19][CH2:20][CH2:23][CH2:56][CH3:57])=[O:18])[C:11]=3[CH:10]=2)[CH:29]=[CH:30][C:31]=1[O:38][CH2:39][CH2:40][CH2:41][O:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:35]
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

9

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 59418692tert-Butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-4H-1,4-benzoxazine-4-carboxylateHCID 59418768HCID 59418768、化合物

生成物 2

HCID 59418702tert-butyl 6-(6-(methoxycarbonyl)-5-(3-phenoxypropoxy)pyridin-2-yl)-2H-benzo[b][1,4]oxazine-4(3H)-carboxylate
HCID 86643667
HCID 86643667、化合物

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 178418476HCID 178418476、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

A mixture of tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazine-4(3H)-carboxylate (53B) (72 mg, 0.20 mmol), methyl 6-bromo-3-(3-phenoxypropoxy)picolinate (26C) (72 mg, 0.20 mmol), K2CO3 (30 mg, 0.22 mmol in 0.5 mL of water), tetrabutyl ammonium bromide (64 mg, 0.20 mmol) and dichlorobis(triphenylphosphine)palladium (II) (10 mg, catalytic amount) in 1,4-dioxane (5 mL) was heated to 90° C. for 6 hours. The reaction mixture was cooled to rt, diluted with EtOAc, filtered through Celite, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with 20% EtOAc in hexanes to provide the desired product tent-butyl 6-(6-(methoxycarbonyl)-5-(3-phenoxypropoxy)pyridin-2-yl)-2H-benzo[b][1,4]oxazine-4(3H)-carboxylate (53C). 1H NMR (300 MHz, CDCl3): 8.49 (1H, s), 7.74 (1H, d), 7.60 (1H, d), 7.38 (1H, d), 7.24 (2H, m), 6.90 (4H, m), 4.31 (2H, t), 4.18 (2H, t), 4.25 (2H, t), 3.95 (3H, s), 3.85 (2H, t), 2.3 (2H, m), 1.58 (9H, s). LCMS (APCI): m/z 521.1 (M+H).

後処理

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered through Celite
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by column chromatography on silica gel eluting with 20% EtOAc in hexanes

出典と根拠

ORDレコード
ord-7a2b285ee4854eeeafad3810644b9f34
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08114893B2

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