HCID 58201773, compound → HCID 58201811, compound

HRID 1964483Notes

Reaction equation

HRID 1964483 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 58201773HCID 58201773, compound

Product 1

HCID 58201811HCID 58201811, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-2-(1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-6-fluoro-5-nitro-1H-indol-2-yl)-2-methylpropan-1-ol (500 mg, 1.4 mmol) was dissolved ethanol (15 mL) and the reaction was flushed with N2. Then Pd—C (50 mg, 5% wt) was added. The reaction was flushed with nitrogen again and then stirred under H2 (atm). After 1 hour only partial conversion to the product was observed by LCMS. The reaction was filtered through Celite and concentrated. The residue was resubjected to the conditions above. After 1 hour 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 (420 mg, 91%). ESI-MS m/z calc. 336.2, found 337.5 (M+1)+. Retention time 0.90 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), 4.78 (br s, 1H), 4.46 (s, 2H), 4.41-4.27 (m, 3H), 4.06(dd, J=6.1, 8.3 Hz, 1H), 3.70-3.67 (m, 1H), 3.53 (dd, J=10.7, 17.2 Hz, 2H), 1.40 (s, 3H), 1.32 (s, 6H) and 1.21 (s, 3H) ppm.

Workup

  1. customthe reaction was flushed with N2
  2. additionThen Pd—C (50 mg, 5% wt) was added
  3. customThe reaction was flushed with nitrogen again
  4. filtrationThe reaction was filtered through Celite
  5. concentrationconcentrated
  6. waitAfter 1 hour LCMS indicated complete
  7. filtrationThe reaction mixture was filtered through Celite
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-aaba81c399974d1d87e40c0ce5571e97
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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