HCID 86713389, compound → HCID 86713390, compound

HRID 921271Notes

Reaction equation

HRID 921271 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:11]([N+:22]([O-])=O)=[C:12]([CH:19]=[CH:20][CH:21]=1)[C:13]([N:15]([O:17][CH3:18])[CH3:16])=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[NH2:22][C:11]1[C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])=[CH:21][CH:20]=[CH:19][C:12]=1[C:13]([N:15]([O:17][CH3:18])[CH3:16])=[O:14]

Participants

4

Reactant 1

HCID 86713389HCID 86713389, compound

Product 1

HCID 86713390HCID 86713390, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Intermediate 37D (1.25 g, 3.53 mmol) and 10% Pd/C (200 mg, 0.188 mmol) in EtOAc (50 mL) was purged with hydrogen. The mixture was then stirred under a hydrogen atmosphere for 1.5 h. The suspension was filtered, and the filtrate was concentrated to dryness. The crude material was purified by flash chromatography (SiO2, 24 g column, EtOAc/hexane=0-40%) to afford Intermediate 37E (939 mg, 82%). HPLC: RT=2.986 min (CHROMOLITH® SpeedROD column 4 6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 mL/min, monitoring at 220 nm), MS(ES): m/z=325.2 [M+H+]; 1H NMR (400 MHz, chloroform-d) δ 7.32 (dd, J=7.7, 1.5 Hz, 1H), 7.11 (dd, J=7.5, 1.5 Hz, 1H), 6.68-6.62 (m, 1H), 5.21 (br. s., 2H), 4.71 (s, 2H), 3.61 (s, 3H), 3.36 (s, 3H), 0.92 (s, 9H), 0.09 (s, 6H).

Workup

  1. customwas purged with hydrogen
  2. filtrationThe suspension was filtered
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe crude material was purified by flash chromatography (SiO2, 24 g column, EtOAc/hexane=0-40%)

Sources & evidence

ORD record
ord-149ddc11a13f40ca9e9cbf2b659da7a5
Source dataset
uspto-grants-2016_03
Patent number
US09273014B2

Reaction notes

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