Cesium carbonate → methyl 6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 1912531

反応式

HRID 1912531 の反応式
[NH2:1][C:2]1[C:11]([CH:12]=O)=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:21])[N:3]=1.[C:22]([O-])([O-])=O.[Cs+].[Cs+].[Si](C=[N+]=[N-])(C)(C)C>CO>[CH3:21][C:4]1[N:3]=[C:2]2[NH:1][CH:22]=[CH:12][C:11]2=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:5]=1[C:6]([O:8][CH3:9])=[O:7]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 167693TrimethylsilyldiazomethaneHCID 86675739HCID 86675739、化合物

生成物 1

HCID 71209360methyl 6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate収率 89%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of methyl 6-amino-5-formyl-2-methyl-4-(p-tolyl)nicotinate (2.45 g, 8.62 mmol) and Cs2CO3 (5.62 g, 17.23 mmol) in methanol (70 ml) was treated with TMS-diazomethane (2M in hexane) (17.23 ml, 34.5 mmol) dropwise at 60° C. The mixture was stirred at 60° for 1 hour, cooled to rt, quenched with sat NH4Cl, extracted with EtOAc, washed with water, Brine, dried with Na2SO4, filtered, and concentrated to afford methyl 6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (2.15 g, 7.67 mmol, 89% yield): 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.86 (br. s., 1 H), 7.40 (d, J=8.1 Hz, 2 H), 7.31-7.26 (m, 3 H), 6.43 (dd, J=2.0, 3.5 Hz, 1 H), 3.64 (s, 3 H), 2.71 (s, 3 H), 2.43 (s, 3 H); LCMS (m/z) ES+=281 (M+1).

後処理

  1. customquenched with sat NH4Cl
  2. extractionextracted with EtOAc
  3. washwashed with water, Brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-53e1759c4fab4f8da6c8e09e6217b612
出典データセット
uspto-grants-2013_12
特許番号
US08609653B2

関連ノート

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