Ammonium formate → HCID 68671304, compound

HRID 1526014Notes

Reaction equation

HRID 1526014 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:53]=[C:54]([F:56])[CH:55]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[N:10]=[C:9]2[NH:34][C:35](=[O:52])[C:36]1[CH:41]=[CH:40][C:39]([N:42]2[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]2)=[CH:38][C:37]=1[N+:49]([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:49][C:37]1[CH:38]=[C:39]([N:42]2[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]2)[CH:40]=[CH:41][C:36]=1[C:35]([NH:34][C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([CH2:5][C:4]3[CH:53]=[C:54]([F:56])[CH:55]=[C:2]([F:1])[CH:3]=3)[CH:7]=2)[N:11]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)=[O:52]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68672067HCID 68672067, compound

Product 1

HCID 68671304HCID 68671304, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-[5-(3,5-difluoro-benzyl)-1-trityl-1H-indazol-3-yl]-4-(4-methyl-piperazin-1-yl)-2-nitro-benzamide (170 mg, 0.236 mmol), 10% Pd—C (10 mg) and ammonium formate (25 mg, 0.4 mmol) in methanol (5 mL) was stirred for 18 hours at room temperature. The catalyst was filtered off and the solution was concentrated. The residue was dissolved in dichloromethane, washed with aqueous solution of NaHCO3, dried and concentrated to yield title compound (145 mg, 87%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe solution was concentrated
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with aqueous solution of NaHCO3
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8a0d23b6f2314b22935426b58a834f38
Source dataset
uspto-grants-2015_07
Patent number
US09085558B2

Reaction notes

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