Dichloromethane → HCID 68465366, compound

HRID 501182Notes

Reaction equation

HRID 501182 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH:4]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([C:27]1[CH:28]=[N:29][C:30]([N:33]2[CH2:45][CH2:44][C:43]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[N:36]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C:35]=3[CH2:34]2)=[N:31][CH:32]=1)=O.[CH2:53](Cl)Cl>>[CH3:1][O:2][C:3](=[O:24])/[CH:4]=[CH:53]/[C:27]1[CH:28]=[N:29][C:30]([N:33]2[CH2:45][CH2:44][C:43]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[N:36]([C:46]([O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:47])[C:35]=3[CH2:34]2)=[N:31][CH:32]=1

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 86607542HCID 86607542, compound

Product 1

HCID 68465366HCID 68465366, compoundYield 78%

Procedure

To a stirred solution methyl(triphenylphosphoranylidene)acetate (2.39 g, 0.0071 moles) in dry DCM (20 mL) was added tert-butyl 2-[5-(formyl)pyrimidin-2-yl]-1,2,3,4-tetrahydro-9H-b-carboline-9-carboxylate (1.35 g, 0.0036 moles) at 0° C. in dry DCM (10 mL). After stirring for >12 hours, the reaction mixture was washed with 10% NaHCO3 solution (20 mL), brine (20 mL), dried (Na2SO4) and concentrated. The compound was purified through silica gel column chromatography using 15% EtOAc in hexane to give tert-butyl 2-{5-[(1E)-3-methoxy-3-oxoprop-1-enyl]pyrimidin-2-yl}-1,2,3,4-tetrahydro-9H-b-carboline-9-carboxylate (1.22 g, 78% yield). 1H NMR (DMSO-d6, 400 MHz) ppm: 8.81 (s, 2H, 2Ar—H), 8.06 (d, 1H, J=8 Hz, 1Ar—H), 7.54 (d, 1H, J=16 Hz, ═CH), 7.50 (d, 1H, J=8 Hz, 1Ar—H), 7.32-7.23 (m, 2H, 2Ar—H), 6.60 (d, 1H, J=16 Hz, —CH), 5.23 (s, 2H, CH2), 4.19 (t, 2H, CH2), 3.7 (s, 3H, OMe), 2.78 (brs, 2H, CH2), 1.68 (s, 9H, 3CH3). M/e=435 (M+1) (M, 434.488 Calcd. for C24H26N4O4).

Workup

  1. washthe reaction mixture was washed with 10% NaHCO3 solution (20 mL), brine (20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe compound was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-ec1cc28a311a467386f613f66ed78472
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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