HCID 58677658, compound → HCID 58677571, compound

HRID 1012643Notes

Reaction equation

HRID 1012643 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][CH2:26][OH:27])[CH:20]=[CH:19][C:18]=3[CH3:28])=[O:16])=[C:11]([N+:29]([O-])=O)[CH:10]=2)=[C:4]([CH3:32])[CH:3]=1>CO.[Pd]>[NH2:29][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[CH3:32])[CH:14]=[CH:13][C:12]=1[C:15]([C:17]1[CH:22]=[C:21]([O:23][CH2:24][CH2:25][CH2:26][OH:27])[CH:20]=[CH:19][C:18]=1[CH3:28])=[O:16]

Participants

4

Reactant 1

HCID 58677658HCID 58677658, compound

Product 1

HCID 58677571HCID 58677571, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 299 (0.026 g, 0.059 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) 1:1→3:1 as the eluent. This afforded the title compound. 1H NMR (CDCl3) δ 7.18 (dd, 1H), 7.11 (d, 1H), 7.03 (d, 1H), 7.00-6.80 (m, 3H), 6.76 (d, 1H), 6.45 (bs, 2H), 5.89 (dd, 1H), 5.75 (d, 1H), 5.59 (s, 1H), 4.08 (t, 2H), 3.83 (t, 2H), 2.22 (s, 3H), 2.18 (s, 3H), 2.01 (m, 2H)

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-02ff18011d4243579e9f45c41716b3a1
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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