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Potassium Fluoride → Tert-butyl 4-[2-(4-carbamoyl-3-fluorophenyl)benzo[d]oxazol-5-yl]piperidine-1-carboxylate

HRID 710184
ノート
印刷プレビュー

反応式

HRID 710184 の反応式
Br[C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)=[CH:7][C:5]=2[N:6]=1.[F:24][C:25]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[CH:30][C:26]=1[C:27]([NH2:29])=[O:28].[F-].[K+]>CN(C=O)C.O>[C:27]([C:26]1[CH:30]=[CH:31][C:32]([C:2]2[O:3][C:4]3[CH:10]=[CH:9][C:8]([CH:11]4[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]4)=[CH:7][C:5]=3[N:6]=2)=[CH:33][C:25]=1[F:24])(=[O:28])[NH2:29]
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

6

反応物 3

HCID 522689Potassium FluorideHCID 590230642-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 71089553Tert-butyl 4-(2-bromobenzo[d]oxazol-5-yl)piperidine-1-carboxylate

生成物 1

HCID 71114235Tert-butyl 4-[2-(4-carbamoyl-3-fluorophenyl)benzo[d]oxazol-5-yl]piperidine-1-carboxylate収率 6.8%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

Intermediate 52 (40 mg, 0.1 mmol), 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (30 mg, 0.12 mmol) and KF (18 mg, 0.3 mmol) were dissolved in a mixture of DMF (1 ml) and water (0.4 ml). This mixture was purged with N2 for 30 mins. Pd(dppf)Cl2.CH2Cl2 was added to the above mixture and again purged with N2 for 30 mins. This reaction mixture was heated to 90° C. for 12 h. Work up (EtOAc and H2O) followed by purification on combiflash using a gradient mixture of EtOAc and Petether (55:45) as eluent afforded the titled compound (3 mg) as an Off-White solid. MS (m/z): 439.5 [M+H]+.

後処理

  1. customThis mixture was purged with N2 for 30 mins
  2. additionCH2Cl2 was added to the above mixture
  3. customagain purged with N2 for 30 mins
  4. customfollowed by purification on combiflash
  5. additiona gradient mixture of EtOAc and Petether (55:45) as eluent

出典と根拠

ORDレコード
ord-a4e88227929c4baa96da9e58a369b016
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181214B2

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