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Triethylamine → tert-butyl 2-carbamoyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

HRID 627016
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HRID 627016 반응식
[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[CH2:10][CH:9]1[C:17]([O-:19])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].C(=O)(O)[O-].[NH4+].C[N:27](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.C([O-])(O)=O.[Na+].[OH-].[Na+]>[C:17]([CH:9]1[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[CH2:10]1)(=[O:19])[NH2:27]
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참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 14013Ammonium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118380491lithium 1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

생성물 1

HCID 118380479tert-butyl 2-carbamoyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate
수율 102.7%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 14798Sodium Hydroxide용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a suspension of lithium 1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (100 mg, 370 μmol, Eq: 1.00) in DMF (5.00 mL) was added sequentially ammonium bicarbonate (90.0 mg, 1.14 mmol, Eq: 3.08), HATU (210 mg, 552 μmol, Eq: 1.49) and triethylamine (100 μL, 717 μmol, Eq: 1.94). The resulting dark yellow mixture was stirred at rt for 2 h. The reaction mixture was diluted with saturated aqueous NaHCO3 (10 mL) and 1 M aqueous NaOH (0.5 mL) and extracted with DCM. The combined organic layers were dried (Na2SO4) and concentrated in vacuo, using n-heptane to azeotrope off residual DMF. The resulting residue was purified by flash chromatography (silica gel, 12 g, 0% to 10% MeOH in DCM) to give tert-butyl 2-carbamoyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate as a white solid (100 mg), m/z=264 (M+H).

후처리

  1. extractionextracted with DCM
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by flash chromatography (silica gel, 12 g, 0% to 10% MeOH in DCM)

출처 및 근거

ORD 기록
ord-918c9b286384419ca3f786afd28a077c
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09309248B2

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