Sodium Methoxide → 4-(1,5-Naphthyridin-4-ylthio)benzenamine

HRID 1013662ノート

反応式

HRID 1013662 の反応式
C[O-].[Na+].Br[C:5]1[CH:14]=[C:13]2[C:8]([C:9]([S:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)=[CH:10][CH:11]=[N:12]2)=[N:7][CH:6]=1>CN(C=O)C.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>[N:12]1[C:13]2[C:8](=[N:7][CH:6]=[CH:5][CH:14]=2)[C:9]([S:15][C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)=[CH:10][CH:11]=1

参加物

5

反応物 2

HCID 10942334Sodium MethoxideHCID 673180344-(7-Bromo-1,5-naphthyridin-4-ylthio)benzenamine

生成物 1

HCID 594273014-(1,5-Naphthyridin-4-ylthio)benzenamine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of tetrakis(triphenylphosphine)palladium (188 mg, 163 μmol) and sodium methoxide (176 mg, 3251 μmol) was added a solution of 4-(7-bromo-1,5-naphthyridin-4-ylthio)benzenamine (540 mg, 1625 μmol) in DMF (2 mL). The resealable tube was purged with argon, and the mixture was heated to 100° for 1.5 h. The mix was diluted with ethyl acetate, washed with brine twice, dried with sodium sulfate, and concentrated. The residue was purified by silica gel chromatography using 1-10% MeOH:CH2Cl2 w/1% NH4OH to provide 4-(1,5-naphthyridin-4-ylthio)benzenamine. MS m/z=254 [M]+. Calc'd for C14H11N3S: 253.32.

後処理

  1. customThe resealable tube was purged with argon
  2. temperaturethe mixture was heated to 100° for 1.5 h
  3. additionThe mix was diluted with ethyl acetate
  4. washwashed with brine twice
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-02ce87d319464250ab2ad5a249b746db
出典データセット
uspto-grants-2011_07
特許番号
US07981891B2

反応ノート

読み込み中…