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Hydrochloric Acid → 6-(3-Chloro-phenyl)-5-cyclopentyl-pyridine-2-carboxylic acid

HRID 927518
ノート
印刷プレビュー

反応式

HRID 927518 の反応式
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:7](Br)[N:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.Cl>O.CN(C=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(Cl)Cl.[Pd](Cl)Cl>[Cl:23][C:24]1[CH:29]=[C:28]([C:7]2[N:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:10]=[CH:9][C:8]=2[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:27]=[CH:26][CH:25]=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 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 866747646-Bromo-5-cyclopentyl-pyridine-2-carboxylic acid methyl ester

生成物 1

HCID 710875526-(3-Chloro-phenyl)-5-cyclopentyl-pyridine-2-carboxylic acid収率 20.5%

試薬・触媒・溶媒 3

HCID 178418807
HCID 178418807、化合物
触媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

6-Bromo-5-cyclopentyl-pyridine-2-carboxylic acid methyl ester (0.6 g, 2.1 mmol), bis(diphenylphosphino)ferrocene-palladium(II)dichloride methylene chloride complex (CAN 95464-05-4, 90 mg, 0.11 mmol) and potassium carbonate (0.37 g, 2.68 mmol) were added to a solution of 3-chlorophenylboronic acid (CAN 63503-60-6, 0.42 g, 2.69 mmol) in water (20 mL) and DMF (2 mL). The mixture was stirred for 48 h at 100° C. Its pH was adjusted to pH=3 with diluted hydrochloric acid. The mixture was extracted with methylene chloride (3×20 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure to give the title compound (130 mg, 20%) which was used in the next step without further purification; MS (EI): m/e=302.0 [M+H]+.

後処理

  1. extractionThe mixture was extracted with methylene chloride (3×20 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f5a7280693d34bc1a0fda956581c009c
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09290451B2

反応ノート

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