1,2-Dimethoxyethane → HCID 178515614、化合物

HRID 33554

反応式

HRID 33554 の反応式
Br[C:2]1[CH:22]=[CH:21][C:5]2[NH:6][C:7]([NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[C:14]4[C:19]=3[CH:18]=[C:17]([OH:20])[CH:16]=[CH:15]4)=[N:8][C:4]=2[CH:3]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])([O-])=O.[Na+].[Na+].O.C(COC)OC>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.CCO>[C:23]1([C:2]2[CH:22]=[CH:21][C:5]3[NH:6][C:7]([NH:9][C:10]4[CH:11]=[CH:12][CH:13]=[C:14]5[C:19]=4[CH:18]=[C:17]([OH:20])[CH:16]=[CH:15]5)=[N:8][C:4]=3[CH:3]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

8

反応物 4

HCID 80711,2-DimethoxyethaneHCID 66827Phenylboronic AcidHCID 2735133Sodium Carbonate MonohydrateHCID 178515612HCID 178515612、化合物

生成物 1

HCID 178515614HCID 178515614、化合物

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒2 回

実験手順

A mixture of 8-(5-bromo-1H-benzo[d]imidazol-2-ylamino)naphthalen-2-ol (18 mg, 0.05 mmol, Example 14), phenylboronic acid (12 mg, 0.1 mmol, Aldrich), PdCl2(PPh3)2 (3.5 mg, 0.005 mmol, Aldrich), Na2CO3.H2O (12 mg, 0.1 mmol), dimethoxyethane (0.35 mL), H2O (0.15 mL) and EtOH (0.1 1 mL) was subjected to microwave irradiation at 120° C. with stirring for 10 min. The reaction mixture was cooled to room temperature, diluted with water (5 mL) and extracted with EtOAc (2×10 mL). The combined organic phases were washed with brine (10 mL), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile) to give the title compound. MS (ESI, pos. ion) m/z: 352 (M+1).

後処理

  1. customirradiation at 120° C.
  2. extractionextracted with EtOAc (2×10 mL)
  3. washThe combined organic phases were washed with brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile)

出典と根拠

ORDレコード
ord-3540a1b0460743118b842ff193bedd8a
出典データセット
uspto-grants-2008_09
特許番号
US07429608B2

関連ノート

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