Pyruvic Acid → 5-(methoxycarbonyl)-1H-pyrrolo(3,2-b)pyridine-2-carboxylic acid

HRID 526012ノート

反応式

HRID 526012 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:31]([OH:36])(=[O:35])[C:32]([CH3:34])=O.C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:11][O:10][C:8]([C:5]1[N:6]=[C:7]2[CH:34]=[C:32]([C:31]([OH:36])=[O:35])[NH:1][C:2]2=[CH:3][CH:4]=1)=[O:9]

参加物

7

反応物 4

HCID 1060Pyruvic AcidHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 12457877Methyl 5-aminopyridine-2-carboxylate

生成物 1

HCID 692267105-(methoxycarbonyl)-1H-pyrrolo(3,2-b)pyridine-2-carboxylic acid

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Methyl 5-aminopyridine-2-carboxylate (1.2 g, 5.2 mmol) and triphenylphosphine (1.5 g, 5.7 mmol) were initially charged in 10 ml of DMF, and pyruvic acid (1.83 g, 20.8 mmol), palladium(II) acetate (279 mg, 1.2 mmol) and triethylamine (2.6 g, 26 mmol) were added. The reaction mixture was stirred at a temperature of 100° C. for four hours, then cooled, concentrated on a rotary evaporator and taken up in ethyl acetate, water was added and the mixture was shaken. The aqueous phase was concentrated on a rotary evaporator and then triturated with a little cyclohexane. This gave 0.5 g (38% of theory) of 5-(methoxycarbonyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid. HPLC-MS: log P=0.44; mass (m/z): 221.0 (M+H)+; 1HNMR (D6-DMSO): δ 3.89 (s, 3H), 7.20 (s, 1H), 7.90-7.98 (m, 2H), 10 (broad, 1H), 12.24 (s, 1H).

後処理

  1. temperaturecooled
  2. concentrationconcentrated on a rotary evaporator
  3. additionwater was added
  4. stirringthe mixture was shaken
  5. concentrationThe aqueous phase was concentrated on a rotary evaporator
  6. customtriturated with a little cyclohexane

出典と根拠

ORDレコード
ord-bc6851da7346401ba853887ee8b2972f
出典データセット
uspto-grants-2016_05
特許番号
US09345247B2

反応ノート

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