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

HRID 389207

반응식

HRID 389207 반응식
[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

참가 물질

8

반응물 4

HCID 80711,2-DimethoxyethaneHCID 25953Cesium fluorideHCID 121872021-Bromo-4-iodo-2-methoxybenzene2회HCID 441187662-Amino-4-cyanobenzeneboronic acid hydrochloride

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f67ab53650414a3d9211dda5317f50ee
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377874B2

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