HCID 58677566, compound → HCID 58677517, compound

HRID 1012648Notes

Reaction equation

HRID 1012648 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:17]3[CH:22]=[C:21]([O:23][CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[CH:20]=[CH:19][C:18]=3[CH3:32])=[O:16])=[C:11]([N+:33]([O-])=O)[CH:10]=2)=[C:4]([CH3:36])[CH:3]=1>CO.[Pd]>[NH2:33][C:11]1[CH:10]=[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[CH3:36])[CH:14]=[CH:13][C:12]=1[C:15]([C:17]1[CH:22]=[C:21]([O:23][CH2:24][CH2:25][N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)[CH:20]=[CH:19][C:18]=1[CH3:32])=[O:16]

Participants

4

Reactant 1

HCID 58677566HCID 58677566, compound

Product 1

HCID 58677517HCID 58677517, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 304 (0.041 g, 0.083 mmol) was dissolved in MeOH (2 mL). A catalytic amount of palladium on charcoal was added and the mixture was stirred under a hydrogen atmosphere for 1 h. The suspension was filtered and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc/petroleum ether (40-60) 3:1→6:1 as the eluent. This afforded the title compound. 1H NMR (CDCl3) δ 7.19 (dd, 1H), 7.1.1 (d, 1H), 7.03 (d, 1H), 7.00-6.80 (m, 3H), 6.76 (d, 1H), 6.46 (bs, 2H), 5.89 (dd, 1H), 5.75 (d, 1H), 5.60 (s, 1H), 4.07 (t, 2H), 3.71 (m, 4H), 2.77 (t, 2H), 2.55 (m, 4H), 2.23 (s, 3H), 2.18 (s, 3H)

Workup

  1. filtrationThe suspension was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-6c1bd23fb8bf4a9ea0f376d2325cd187
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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