Trifluoroacetic acid methylene chloride → 4-(1H-pyrrolo(2,3-b)pyridin-3-yl)piperidine

HRID 1370042Notes

Reaction equation

HRID 1370042 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[NH:8]1[CH2:9][CH2:10][CH:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:12][CH2:13]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 49758876tert-butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate

Product 1

HCID 55294774-(1H-pyrrolo(2,3-b)pyridin-3-yl)piperidineYield 151.2%

Procedure

4-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-piperidine-1-carboxylic acid tert-butyl ester (963 mg, 3.2 mmol) was set stirring in 1:1 TFA/CH2Cl2. After 45 min the mixture was evaporated and the golden oil brought up in Et2O. A solid formed and was filtered, washed with Et2O and air dried to give 974 mg (96%) of a white solid as a TFA salt. MS (electrospray): exact mass calculated for C12H15N3, 201.13; m/z found, 202.1 [M++H]. 1H NMR (CDCl3, 400 MHz): 8.09 (dd, J=3.33 Hz, 1.57 Hz, 1H), 7.89 (dd, J=6.26 Hz, 1.57 Hz, 1H), 7.01 (s, 1H), 6.99 (dd, J=4.89 Hz, 3.13 Hz, 1H), 5.04 (br s, 2H), 3.11-3.04 (m, 2H), 2.88-2.79 (m, 1H), 2.73-2.64 (m, 2H), 1.94 (d, J=12.52 Hz, 2H), 1.65-1.63 (m, 2H).

Workup

  1. customAfter 45 min the mixture was evaporated
  2. customA solid formed
  3. filtrationwas filtered
  4. washwashed with Et2O and air
  5. customdried

Sources & evidence

ORD record
ord-f54de8522bda4db1bcdda7b337e772a2
Source dataset
uspto-grants-2003_06
Patent number
US06579896B2

Reaction notes

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