Dichloromethane → (3-chloro-benzyl)-[5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-methyl-1H-pyrazol-3-yl]-amine

HRID 1024323Notes

Reaction equation

HRID 1024323 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][CH:37]=1)[CH2:5][NH:6][C:7]1[CH:8]=[C:9]([CH:13]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([Cl:24])[CH:22]=3)[N:17]([Si](C(C)C)(C(C)C)C(C)C)[CH:16]=2)O)[N:10]([CH3:12])[N:11]=1.ClCCl.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][CH:37]=1)[CH2:5][NH:6][C:7]1[CH:8]=[C:9]([CH2:13][C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([Cl:24])[CH:22]=3)[NH:17][CH:16]=2)[N:10]([CH3:12])[N:11]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 66971157[5-(3-chloro-benzylamino)-2-methyl-2H-pyrazol-3-yl]-(5-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

Product 1

HCID 24954651(3-chloro-benzyl)-[5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-methyl-1H-pyrazol-3-yl]-amineYield 17.1%

Procedure

[5-(3-Chloro-benzylamino)-2-methyl-2H-pyrazol-3-yl]-(5-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (649, 0.033 g, 0.059 mmol) was combined with dichloromethane (5 mL, 0.08 mol) and triethylsilane (200 μL, 1.0 mmol) was added, followed by trifluoroacetic acid (100 μL, 1.0 mmol). The reaction was stirred at room temperature overnight and then concentrated. Ethyl acetate was added and the organic portion was washed with 1M potassium carbonate, dried over anhydrous sodium sulfate and concentrated. Purification with silica gel flash chromatography eluting with a gradient of methanol (2-20%) and dichloromethane followed by washes with a mixture of ethyl acetate:hexane gave the desired compound (P-0410, 0.0039 g, 17%). (ESI) [M+H+]+=387.30.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. additionEthyl acetate was added
  4. washthe organic portion was washed with 1M potassium carbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customPurification with silica gel flash chromatography
  8. washeluting with a gradient of methanol (2-20%) and dichloromethane
  9. additionfollowed by washes with a mixture of ethyl acetate

Sources & evidence

ORD record
ord-8b835b46a75547da9d3861d8b6e3ee5b
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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