Dimethylformamide → (R)-1-(2-chlorobutanoyl)-3,3-dimethylindoline-6-carbonitrile

HRID 1475533ノート

反応式

HRID 1475533 の反応式
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N([CH2:30][CH3:31])CC)C.[CH3:32][C:33]1([CH3:44])[C:41]2[C:36](=[CH:37][C:38]([C:42]#[N:43])=[CH:39][CH:40]=2)[NH:35][CH2:34]1.CN([CH:48]=[O:49])C.[CH2:50](Cl)[Cl:51]>C(OCC)(=O)C>[Cl:51][C@H:50]([CH2:30][CH3:31])[C:48]([N:35]1[C:36]2[C:41](=[CH:40][CH:39]=[C:38]([C:42]#[N:43])[CH:37]=2)[C:33]([CH3:44])([CH3:32])[CH2:34]1)=[O:49]

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 107023412,3-dihydro-3,3-dimethyl-1H-indole-6-carbonitrile

生成物 1

HCID 86724047(R)-1-(2-chlorobutanoyl)-3,3-dimethylindoline-6-carbonitrile

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of (R)-2-chloro-1-butyric acid (0.47 mL, 4.60 mmol) in DCM was added HBTU (2.18 g, 5.75 mmol). After stirring for 30 min, triethylamine (0.96 mL, 6.9 mmol) and 3,3-dimethyl-2,3-dihydro-1H-indole-6-carbonitrile (0.80 g, 4.6 mmol) were added, the resulting mixture was stirred overnight. A drop of DMF was added and the reaction was stirred overnight. The reaction mixture was then diluted with ethyl acetate and washed with water. The organics were separated, dried with sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 20% ethyl acetate in heptane to give (R)-1-(2-chlorobutanoyl)-3,3-dimethylindoline-6-carbonitrile containing un-reacted 3,3-dimethyl-2,3-dihydro-1H-indole-6-carbonitrile. The mixture was taken up in DCM and washed with 2M HCl solution. The organics were dried with sodium sulfate and concentrated, to give (R)-1-(2-chlorobutanoyl)-3,3-dimethylindoline-6-carbonitrile (0.38 g). 1H NMR (400 MHz, CDCl3) 8.53 (s, 1H), 7.38 (d, 1H), 7.25 (d, 1H), 4.22-4.29 (m, 1H), 4.15 (d, 1H), 3.87 (d, 1H), 2.19-2.04 (m, 2H), 1.39 (s, 6H), 1.09 (t, 3H).

後処理

  1. stirringthe resulting mixture was stirred overnight
  2. stirringthe reaction was stirred overnight
  3. washwashed with water
  4. customThe organics were separated
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel eluting with 20% ethyl acetate in heptane

出典と根拠

ORDレコード
ord-6a19a84b793849aaa07f33d99a3af3b4
出典データセット
uspto-grants-2015_04
特許番号
US09018214B2

反応ノート

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