Water → HCID 59368492, compound

HRID 1481440Notes

Reaction equation

HRID 1481440 reaction equation
CS(O[CH:6]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[F:30])[CH2:7][N:8]1[C:16]2[CH:15]=[CH:14][C:13](Cl)=[CH:12][C:11]=2[C:10]2[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22][C:9]1=2)(=O)=O.O>CO.[Pd]>[F:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:6][CH2:7][N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22][C:9]1=2

Participants

5

Reactant 2

HCID 962WaterHCID 86642474HCID 86642474, compound

Product 1

HCID 59368492HCID 59368492, compoundYield 36.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-(9-Chloro-3-methyl-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)-1-(2-fluorophenyl)ethyl methanesulfonate (530 mg, 0.001177 mol) was dissolved in methanol and 10% Pd—C (62 mg, 0.5885 mmol) was added. A drop of water was added and the reaction mass is stirred at RT for 24 h under hydrogen atmosphere. The reaction mass was filtered through Celite and the filtrate concentrated to obtain the crude compound. The crude was purified by preparative HPLC to obtain 140 mg desired compound. 1H NMR (CDCl3, TFA salt) δ (ppm): 7.60 (s, 1H), 7.30-7.20 (m, 2H), 7.20-7.15 (d, 1H), 7.10-7.00 (t, 12H), 7.00-6.90 (t, 1H), 6.90-6.80 (t, 1H), 4.40-4.30 (t, 2H), 3.90-3.85 (t, 2H), 3.60-3.50 (t, 2H), 3.30-3.10 (m, 4H), 3.10 (t, 2H), 2.90 (s, 3H).

Workup

  1. filtrationThe reaction mass was filtered through Celite
  2. concentrationthe filtrate concentrated
  3. customto obtain the crude compound
  4. customThe crude was purified by preparative HPLC

Sources & evidence

ORD record
ord-0e1d722ccea348fa888d478856593d22
Source dataset
uspto-grants-2016_08
Patent number
US09409910B2

Reaction notes

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