Ammonium formate → HCID 10542998, compound

HRID 1459706Notes

Reaction equation

HRID 1459706 reaction equation
C([NH:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([N:26]4[CH:30]=[N:29][N:28]=[CH:27]4)[CH:24]=3)[NH:19][CH:18]=2)[CH2:11]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([N:26]4[CH:27]=[N:28][N:29]=[CH:30]4)[CH:24]=3)[NH:19][CH:18]=2)[CH2:11]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 10386282HCID 10386282, compound

Product 1

HCID 10542998HCID 10542998, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of (3S)-3-(N-benzyl)aminomethyl-1-[2-(5-(1,2,4-triazol-4-yl)-1H-indol-3-yl)ethyl]pyrrolidine (Example 7; 0.277 g, 0.639 mmol), ammonium formate (0.218 g, 3.46 mmol) and 10% Pd-C (0.28 g), in anhydrous methanol (20 ml) was stirred at 62° C. for 0.75 h. The mixture was cooled to 25° C. and the catalyst removed filtration through celite. The solvent was removed under vacuum and the residue chromatographed on silica gel eluting with CH2Cl2 /MeOH/NH3 (20:8:1) to give the title compound (0.145 g, 68%), δ (250 MHz, CDCl3) 1.48-1.59 (1H, m, CH of CH2), 2.03-2.14 (1H, m, CH of CH2), 2.29-2.41 (2H, m, 2 of CH), 2.63-3.02 (9H, m, 4 of CH2 and CH), 7.14 (1H, dd, J=2.1 and 8.6 Hz, Ar--H), 7.21 (1H, s, Ar--H), 7.49 (1H, d, J=8.6 Hz, Ar--H), 7.60 (1H, d, J=2.1 Hz, Ar--H), 8.54 (2H, s, Ar--H).

Workup

  1. customthe catalyst removed
  2. filtrationfiltration through celite
  3. customThe solvent was removed under vacuum
  4. customthe residue chromatographed on silica gel eluting with CH2Cl2 /MeOH/NH3 (20:8:1)

Sources & evidence

ORD record
ord-fc932c142bc14bbb8c656b913602b03a
Source dataset
uspto-grants-1998_12
Patent number
US05854268

Reaction notes

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