1,2-Dimethoxyethane → 2-Amino-4'-bromo-3'-methoxybiphenyl-4-carbonitrile

HRID 389207

反応式

HRID 389207 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[O:9][CH3:10].[F-].[Cs+].Cl.[NH2:14][C:15]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:16]=1B(O)O.COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.CCOC(C)=O>[NH2:14][C:15]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:16]=1[C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([O:9][CH3:10])[CH:4]=1

参加物

8

反応物 4

HCID 80711,2-DimethoxyethaneHCID 25953Cesium fluorideHCID 121872021-Bromo-4-iodo-2-methoxybenzene2 回HCID 441187662-Amino-4-cyanobenzeneboronic acid hydrochloride

生成物 1

HCID 594088822-Amino-4'-bromo-3'-methoxybiphenyl-4-carbonitrile

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a mixture of the product from Step 1, -bromo-4-iodo-2-methoxybenzene (750 mg, 2.4 mmol), CsF (1.09 g, 7.2 mmol), (2-amino-4-cyanophenyl)boronic acid hydrochloride (390 mg, 2.4 mmol), and Pd(PPh3)4 (277 mg, 0.24 mmol) was added DME (15 mL) under nitrogen. It was then heated to 100° C. After 36 hours, EtOAc and water were added to the resulting thick red suspension. The organic layer was washed with brine, dried over Na2SO4, and the solvent was removed in vacuo. The residue was purified on silica (gradient elution, 3-50% EtOAc/hexanes) to yield the title compound as a red oil. LRMS (M+H)+=303.1.

後処理

  1. washThe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified on silica (gradient elution, 3-50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-f67ab53650414a3d9211dda5317f50ee
出典データセット
uspto-grants-2013_02
特許番号
US08377874B2

関連ノート

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