{2-[1-(tert-Butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonyl]-5-chloro-pyridin-3-yl}-(4-methoxy-benzyl)-carbamic acid tert-butyl ester → (3-Amino-5-chloro-pyridin-2-yl)-(1H-pyrrolo[2,3-b]pyridin-4-yl)-methanone

HRID 1898230Notes

Reaction equation

HRID 1898230 reaction equation
C(OC(=O)[N:7]([C:17]1[C:18]([C:24]([C:26]2[C:27]3[CH:34]=[CH:33][N:32]([Si](C(C)(C)C)(C)C)[C:28]=3[N:29]=[CH:30][CH:31]=2)=[O:25])=[N:19][CH:20]=[C:21]([Cl:23])[CH:22]=1)CC1C=CC(OC)=CC=1)(C)(C)C>C(O)(C(F)(F)F)=O>[NH2:7][C:17]1[C:18]([C:24]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]3[NH:32][CH:33]=[CH:34][C:27]=23)=[O:25])=[N:19][CH:20]=[C:21]([Cl:23])[CH:22]=1

Participants

3

Reactant 1

HCID 58268119{2-[1-(tert-Butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonyl]-5-chloro-pyridin-3-yl}-(4-methoxy-benzyl)-carbamic acid tert-butyl ester

Product 1

HCID 58268254(3-Amino-5-chloro-pyridin-2-yl)-(1H-pyrrolo[2,3-b]pyridin-4-yl)-methanoneYield 85.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

0.97 g of {2-[1-(tert-Butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonyl]-5-chloro-pyridin-3-yl}-(4-methoxy-benzyl)-carbamic acid tert-butyl ester and desilylated analog mixture was dissolved in 5 mL of TFA, stirred at r.t. for 2 h and evaporated. The residue was partitioned into a mixture of aqueous sodium bicarbonate solution and ethyl acetate. The organic layer was evaporated under reduced pressure. The solid residue was triturated with 200 mL of a 1:3 mixture of ethyl acetate-hexanes to afford 372 mg of the product as a brown solid. LC-MSD, m/z for C13H9ClN4O [M+H]+=273.0, 275.0;

Workup

  1. customevaporated
  2. customThe residue was partitioned into a mixture of aqueous sodium bicarbonate solution and ethyl acetate
  3. customThe organic layer was evaporated under reduced pressure
  4. customThe solid residue was triturated with 200 mL of a 1:3 mixture of ethyl acetate-hexanes

Sources & evidence

ORD record
ord-1d13b4d5823d4a0794a37297fc37daf2
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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