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

HRID 526012노트

반응식

HRID 526012 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bc6851da7346401ba853887ee8b2972f
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09345247B2

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