HCID 118423379, compound → HCID 118414935, compound

HRID 1054314Notes

Reaction equation

HRID 1054314 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][C:7](/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:6][C:5]=2[N:4]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:27][CH:26]=2)[N:3]=1>CCO.C1COCC1.[Pd]>[CH3:1][C:2]1[C:10]2[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][C:7]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:6][C:5]=2[N:4]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:29][CH:30]=2)[N:3]=1

Participants

5

Reactant 1

HCID 118423379HCID 118423379, compound

Product 1

HCID 118414935HCID 118414935, compoundYield 85.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(see, e.g., WO2013039988A1). To a suspension of 10% Pd/C (70 mg) in EtOH (5 mL) was added 52 (186 mg, 0.38 mmol) dissolved in THF (1.5 mL). The suspension was stirred under an atmosphere of hydrogen (ca. 1 atm, balloon) overnight. The suspension was filtered through a pad of celite and the filtrate was concentrated under reduced pressure to provide the title compound (159 mg, 84%) as a light brown oil. Crude was used in the next reaction without further purification. 1H NMR (500 MHz, CDCl3) δ 7.44 (s, 1H), 7.36-7.31 (m, 3H), 7.31-7.26 (m, 3H), 7.26-7.22 (m, 2H), 7.19 (t, J=7.0 Hz, 1H), 7.09 (t, J=7.4 Hz, 1H), 7.00 (d, J=7.9 Hz, 2H), 6.95 (d, J=8.5 Hz, 2H), 5.67 (s, 2H), 4.49 (q, J=7.1 Hz, 2H), 3.35-3.27 (m, 2H), 3.24-3.17 (m, 2H), 2.73 (s, 3H), 1.47 (t, J=7.1 Hz, 3H). 13C NMR (125 MHz, CDCl3) δ 165.85, 161.09, 157.08, 156.78, 152.23, 141.30, 140.97, 133.36, 132.21, 129.72, 129.55, 128.49, 128.41, 126.04, 123.30, 118.95, 118.80, 117.33, 109.68, 61.83, 49.83, 39.82, 35.23, 16.31, 14.30. ESI MS: m/z 516.9 (M+H)+.

Workup

  1. filtrationThe suspension was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-88e9de1a744646dc916b3af345e852da
Source dataset
uspto-grants-2016_07
Patent number
US09394303B2

Reaction notes

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