HCID 59129576, compound → HCID 58201809, compound

HRID 1847601Notes

Reaction equation

HRID 1847601 reaction equation
[CH3:1][C:2]1([CH3:26])[O:6][C@H:5]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([N+:18]([O-])=O)=[C:14]([F:17])[CH:15]=3)[CH:10]=[C:9]2[C:21]([CH3:25])([CH3:24])[CH2:22][OH:23])[CH2:4][O:3]1>C(O)C>[NH2:18][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][C:14]=1[F:17])[N:8]([CH2:7][C@@H:5]1[CH2:4][O:3][C:2]([CH3:1])([CH3:26])[O:6]1)[C:9]([C:21]([CH3:25])([CH3:24])[CH2:22][OH:23])=[CH:10]2

Participants

3

Reactant 1

HCID 59129576HCID 59129576, compound

Product 1

HCID 58201809HCID 58201809, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-2-(1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-6-fluoro-5-nitro-1H-indol-2-yl)-2-methylpropan-1-ol (2.5 g, 6.82 mmol) was dissolved ethanol (70 mL) and the reaction was flushed with N2. Then Pd—C (250 mg, 5% wt) was added. The reaction was flushed with nitrogen again and then stirred under H2 (atm). After 2.5 hours only partial conversion to the product was observed by LCMS. The reaction was filtered through Celite and concentrated. The residue was re-subjected to the conditions above. After 2 hours LCMS indicated complete conversion to product. The reaction mixture was filtered through Celite. The filtrate was concentrated to yield the product as a black solid (1.82 g, 79%). ESI-MS m/z calc. 336.2, found 337.5 (M+1)+. Retention time 0.86 minutes. 1H NMR (400 MHz, DMSO-d6) δ 7.17 (d, J=12.6 Hz, 1H), 6.76 (d, J=9.0 Hz, 1H), 6.03 (s, 1H), 4.79-4.76 (m, 1H), 4.46 (s, 2H), 4.37-4.31 (m, 3H), 4.06 (dd, J=6.1, 8.3 Hz, 1H), 3.70-3.67 (m, 1H), 3.55-3.52 (m, 2H), 1.41 (s, 3H), 1.32 (s, 6H) and 1.21 (s, 3H) ppm.

Workup

  1. customthe reaction was flushed with N2
  2. additionThen Pd—C (250 mg, 5% wt) was added
  3. customThe reaction was flushed with nitrogen again
  4. filtrationThe reaction was filtered through Celite
  5. concentrationconcentrated
  6. waitAfter 2 hours LCMS indicated complete conversion to product
  7. filtrationThe reaction mixture was filtered through Celite
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-bc985e146d8f48829a93ba1f201c303c
Source dataset
uspto-grants-2015_02
Patent number
US08952050B2

Reaction notes

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