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Cesium carbonate → 7-(4-Methoxy-2-methylphenyl)-2,6-dimethyl-N-[(1S)-1-methylpropyl]pyrrolo[1,2-b]pyridazin-4-amine

HRID 1796966
ノート
印刷プレビュー

反応式

HRID 1796966 の反応式
Br[C:2]1[C:3]2[N:4]([C:9]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=3[CH3:21])=[C:10]([CH3:12])[CH:11]=2)[N:5]=[C:6]([CH3:8])[CH:7]=1.[C@@H:22]([NH2:26])([CH2:24][CH3:25])[CH3:23].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:9]2[N:4]3[N:5]=[C:6]([CH3:8])[CH:7]=[C:2]([NH:26][C@@H:22]([CH3:23])[CH2:24][CH3:25])[C:3]3=[CH:11][C:10]=2[CH3:12])=[C:14]([CH3:21])[CH:15]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)2 回HCID 67137532-Butanamine, (S)-2 回HCID 221747864-Bromo-7-(4-methoxy-2-methylphenyl)-2,6-dimethylpyrrolo[1,2-b]pyridazine

生成物 1

HCID 586199647-(4-Methoxy-2-methylphenyl)-2,6-dimethyl-N-[(1S)-1-methylpropyl]pyrrolo[1,2-b]pyridazin-4-amine

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒2 回HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 4-bromo-7-(4-methoxy-2-methylphenyl)-2,6-dimethylpyrrolo[1,2-b]pyridazine (0.137 g, 0.397 mmol), (S)-(+)-sec-butylamine (0.08 mL, 0.794 mmol), xantphos (0.025 g, 0.04 mmol), Cs2CO3 (0.18 g, 0.55 mmol) and Pd2(dba)3 (0.018 g, 0.02 mmol) in dioxane (4.0 mL) was refluxed for 17 h. Extra (S)-(+)-sec-butylamine (0.08 mL, 0.794 mmol), xantphos (0.025 g, 0.04 mmol) and Pd2(dba)3 (0.018 g, 0.02 mmol) were added to the reaction mixture and refluxed for additional 4 h. After cooling to room temperature, the mixture was filtered through a pad of celite. The filtrate was concentrated in vacuo to dryness, the residue was subjected to column chromatography (silica gel, 1/10 EtOAc/heptane) to give 0.024 g (18%) of light yellow oil as the title compound. 1H NMR (300 MHz, CDCl3) δ 7.23 (d, J=11 Hz, 1H), 6.89 (d, J=4 Hz, 1H), 6.83 (dd, J=4, 11 Hz, 1H), 6.29 (br s, 1H), 5.54 (s, 1H), 3.87 (s, 3H), 3.64–3.56 (m, 1H), 2.32 (s, 3H), 2.16 (s, 3H), 2.11 (s, 3H), 1.77–1.57 (m, 2H), 1.32–1.28 (m, 3H), 1.06–0.99 (m, 3H); MS m/z 338.4 (M++H).

後処理

  1. temperaturewas refluxed for 17 h
  2. temperaturerefluxed for additional 4 h
  3. filtrationthe mixture was filtered through a pad of celite
  4. concentrationThe filtrate was concentrated in vacuo to dryness

出典と根拠

ORDレコード
ord-08435f8646144509ad724c50bf3ced46
出典データセット
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07034023B2

反応ノート

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