Triphenylphosphine → HCID 89964282, 화합물

HRID 1846235노트

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HRID 1846235 반응식
C=[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1.C(N(C1C(Br)=NC=CC=1)C(=O)[O:23]C(C)(C)C)C=C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])=O.[K+]>CN(C=O)C.O.[Cl-].C([N+](CC)(CC)CC)C.CCOC(C)=O.C([O-])(O)=O.[Na+].CC([O-])=O.CC([O-])=O.[Pd+2]>[O:23]=[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1

참가 물질

10

반응물 4

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 68559071HCID 68559071, 화합물HCID 89964062HCID 89964062, 화합물

생성물 1

HCID 89964282HCID 89964282, 화합물

시약·촉매·용매 5

HCID 167845palladium(II) acetate촉매HCID 16211205Tetraethylammonium chloride monohydrate촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

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온도
110 °C

실험 절차

tert-butyl 3-methylene-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate. To a solution of tert-butyl allyl(2-bromopyridin-3-yl)carbamate (1 eq.) in DMF (0.2 M), PPh3 (0.25 eq.), Pd(OAc)2 (0.1 eq), and KOAc (5 eq.), is added, under an argon atmosphere, tetraethyl ammonium chloride hydrate (2 eq.). The flask is purged with argon for 15 min, and the resulting reaction mixture is stirred at 110° C. for 16 h. The reaction progress is monitored by TLC. The reaction mixture is diluted with EtOAc and saturated NaHCO3 solution. The organic layer is separated and dried over Na2SO4, and concentrated. The product that may be thus obtained is purified by column chromatography to afford the title compound.

후처리

  1. customThe flask is purged with argon for 15 min
  2. customthe resulting reaction mixture
  3. customThe organic layer is separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe product that may be thus obtained
  7. customis purified by column chromatography

출처 및 근거

ORD 기록
ord-9c565f3a3a3646329a5e7a66f2aef4c7
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952009B2

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