Dimethylformamide → 5-Methoxy-2-methyl-1H-indole-3-carbonitrile

HRID 889901ノート

反応式

HRID 889901 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[CH:6]2.[C:13](#[N:15])C.ClS(N=C=O)(=O)=O.CN(C)C=O>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[C:13]#[N:15]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6342AcetonitrileHCID 706425-Methoxy-2-methylindoleHCID 70918Chlorosulfonyl isocyanate

生成物 1

HCID 222500905-Methoxy-2-methyl-1H-indole-3-carbonitrile収率 67%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a 0° C. solution of 5-Methoxy-2-methyl-1H-indole (5 g, 31.0 mmol), dry acetonitrile, (90 mL) was slowly added chlorosulfonyl isocyanate (3 mL, 34.1 mmol). The reaction was stirred and allowed to warm to room temperature and stirred for an additional four hours followed by the addition of dimethyl formamide (4.8 mL (62.0 mmol)and then stirred for an additional 1.5 hours at room temperature. The reaction was poured into water and extracted with diethyl ether. The aqueous layer was adjusted to pH 9 with 1M potassium carbonate, and extracted with diethyl ether. The ether layers were combined and dried over magnesium sulfate, filtered and concentrated. Crystallization of the residue from ether and hexane gave 5-methoxy-2-methyl-1H-indole-3-carbonitrile (3.86 g) in 67% yield as a light pink solid. C11H10N2O: GC/MS r.t.=4.06 min., m/z 186; 1H NMR (CDCl3): δ 7.22 (d, 1H, J=8.3 Hz), 7.08 (s, 1H), 6.86 (d, 1H, J=8.3 Hz), 3.86 (s, 3H), 2.60 (s, 3H) ppm.

後処理

  1. customTo a 0° C.
  2. stirringstirred for an additional four hours
  3. stirringstirred for an additional 1.5 hours at room temperature
  4. extractionextracted with diethyl ether
  5. extractionextracted with diethyl ether
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customCrystallization of the residue from ether and hexane

出典と根拠

ORDレコード
ord-ef16703b86734a708b928469a1eba742
出典データセット
uspto-grants-2006_02
特許番号
US06995171B2

反応ノート

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