2-[2-(tert-butyldimethylsilanyloxy)propyl]-4,6,7-trichloro-2H-indazole → 2-Amino-2-methyl-3-(4,6,7-trichloro-2H-indazol-2-yl)propionitrile

HRID 2062023Notes

Reaction equation

HRID 2062023 reaction equation
[Cl:1][C:2]1[C:3]2[C:7]([C:8]([Cl:12])=[C:9]([Cl:11])[CH:10]=1)=[N:6][N:5]([CH2:13][C:14](=O)[CH3:15])[CH:4]=2.[Si]([O:24][CH:25]([CH3:39])[CH2:26][N:27]1[CH:35]=[C:34]2[C:29]([C:30]([Cl:38])=[C:31]([Cl:37])[CH:32]=[C:33]2[Cl:36])=[N:28]1)(C(C)(C)C)(C)C.[N+:40](C1C(Cl)=C(Cl)C=C(Cl)C=1C=O)([O-])=O>>[NH2:40][C:14]([CH3:15])([CH2:13][N:5]1[CH:4]=[C:3]2[C:7]([C:8]([Cl:12])=[C:9]([Cl:11])[CH:10]=[C:2]2[Cl:1])=[N:6]1)[C:26]#[N:27].[Cl:36][C:33]1[C:34]2[C:29]([C:30]([Cl:38])=[C:31]([Cl:37])[CH:32]=1)=[N:28][N:27]([CH2:26][C:25](=[O:24])[CH3:39])[CH:35]=2

Participants

5

Reactant 3

HCID 666201752-[2-(tert-butyldimethylsilanyloxy)propyl]-4,6,7-trichloro-2H-indazoleHCID 666207131-(4,6,7-Trichloro-2H-indazol-2-yl)propan-2-oneHCID 866255902-Nitro-3,4,6-trichlorobenzaldehyde

Product 2

HCID 666207131-(4,6,7-Trichloro-2H-indazol-2-yl)propan-2-oneHCID 666208912-Amino-2-methyl-3-(4,6,7-trichloro-2H-indazol-2-yl)propionitrileYield 60%

Procedure

2-Amino-2-methyl-3-(4,6,7-trichloro-2H-indazol-2-yl)propionitrile (0.16 g, 60%) was prepared using a procedure similar to that described in Example 1, part b, except starting from 1-(4,6,7-trichloro-2H-indazol-2-yl)propan-2-one (0.25 g). 1-(4,6,7-Trichloro-2H-indazol-2-yl)propan-2-one was prepared using a procedure similar to that described in Example 105 part c and d except starting from 2-[2-(tert-butyldimethylsilanyloxy)propyl]-4,6,7-trichloro-2H-indazole (1.4 g, 69%) that was prepared using a procedure similar to that described in Example 132 part a except starting from [2-(tert-butyldimethylsilanyloxy)propyl]-(2-nitro-3,4,6-trichlorobenzypamine (2.2 g). [2-(tert-Butyldimethylsilanyloxy)propyl]-(2-nitro-3,4,6-trichlorobenzypamine (2.2 g, 44%) was prepared using a procedure similar to that described in Example 105 part a except starting from 2-nitro-3,4,6-trichlorobenzaldehyde (3 g) that was prepared as follows:

Workup

  1. customwas prepared
  2. custom[2-(tert-Butyldimethylsilanyloxy)propyl]-(2-nitro-3,4,6-trichlorobenzypamine (2.2 g, 44%) was prepared
  3. customwas prepared

Sources & evidence

ORD record
ord-14e18b20ecd64dc48ef136ae9438752d
Source dataset
uspto-grants-2012_10
Patent number
US08283475B2

Reaction notes

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