Tetrahydrofuran → HCID 59161296, compound

HRID 545568Notes

Reaction equation

HRID 545568 reaction equation
C(C1[CH:4]=[C:5]2[C:13](=CC=1)[N:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)[C:11]1[CH2:10][CH2:9][C@@H:8]([NH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[CH2:7][C:6]2=1)#N.[CH3:30][Mg]Br.[O:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>>[C:37]([C:36]1[CH:35]=[C:34]2[C:13](=[CH:5][CH:4]=1)[N:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)[C:11]1[CH2:10][CH2:9][C@@H:8]([NH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[CH2:7][C:6]2=1)(=[O:33])[CH3:30]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 59161298HCID 59161298, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59161296HCID 59161296, compoundYield 74%

Procedure

Treat (R)-N-[6-cyano-9-(3-fluorobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]isobutyramide (Example 123) (2.07 g, 5.32 mmol) with methyl magnesium bromide (9 mL) in refluxing tetrahydrofuran for 18 h. Quench with MeOH, filter to remove the solids, and concentrate in vacuo. Treat the residue with 1N HCl/THF and reflux for 2 h. Add ethyl acetate, filter to remove insoluable precipitate, and concentrate the filtrate in vacuo to give 2.7 g (74%) of a yellow solid. MS (ES): m/z 407 (M+1); HPLC: Rt=2.3 min (97%).

Workup

  1. customQuench with MeOH
  2. filtrationfilter
  3. customto remove the solids
  4. concentrationconcentrate in vacuo
  5. additionTreat the residue with 1N HCl/THF
  6. temperaturereflux for 2 h
  7. filtrationAdd ethyl acetate, filter
  8. customto remove insoluable precipitate
  9. concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-d3bd0818dd3f432883a00c4328e1ecaf
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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