HCID 68465366, compound → HCID 68461476, compound

HRID 501183Notes

Reaction equation

HRID 501183 reaction equation
[CH3:1][O:2][C:3](=[O:32])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[N:8][C:9]([N:12]2[CH2:24][CH2:23][C:22]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:14]=3[CH2:13]2)=[N:10][CH:11]=1.[H][H]>C1COCC1.[Pd]>[C:28]([O:27][C:25]([N:15]1[C:14]2[CH2:13][N:12]([C:9]3[N:8]=[CH:7][C:6]([CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:32])=[CH:11][N:10]=3)[CH2:24][CH2:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:26])([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 2

HCID 68465366HCID 68465366, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68461476HCID 68461476, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 2-{5-[(1E)-3-methoxy-3-oxoprop-1-enyl]pyrimidin-2-yl}-1,2,3,4-tetrahydro-9H-b-carboline-9-carboxylate (0.25 g, 0.0005 moles) (See Example 20) in 10 mL of dry THF was added 1:1 mixture of Pd (OH)2 (50 mg) & Pd/C (50 mg) and stirred in the hydrogen atmosphere using balloon. After stirring for >12 hours, the reaction was filtered through a celite pad. The filtrate was concentrated and the crude residue was purified through silica column using 30% EtOAc in hexane to give methyl 3-{2-[9-(tert-butyloxycarbonyl)-1,3,4,9-tetrahydro-2H-b-carbolin-2-yl]pyrimidin-5-yl}propanoate (0.16 g, 63% yield). 1H NMR (DMSO-d6, 400 MHz) ppm: 8.33 (s, 2H, 2Ar—H), 8.06 (d, 1H, J=8 Hz, 1Ar—H), 7.49 (d, 1H, J=8 Hz, 1Ar—H), 7.31-7.22 (m, 2H, 2Ar—H), 5.12 (s, 2H, CH2), 4.09 (t, 2H, J=8 Hz, CH2), 3.57 (s, 3H, OMe), 2.74 (brs, 2H, CH2), 2.7 (t, 2H, CH2), 2.67 (t, 2H, CH2), 1.68 (s, 9H, 3CH3). M/e=437 (M+1) (M, 436.504 Calcd. for C24H28N4O4).

Workup

  1. filtrationthe reaction was filtered through a celite pad
  2. concentrationThe filtrate was concentrated
  3. customthe crude residue was purified through silica column

Sources & evidence

ORD record
ord-128526d4ce5842658dcbba7eaed956fa
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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