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Hydrochloric Acid → {3-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-(3-trifluoromethyl-pyridin-2-yl)-methanol

HRID 886555
Notes
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Reaction equation

HRID 886555 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([CH:24]([C:26]4[C:31]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:29]=[CH:28][N:27]=4)[OH:25])[CH:21]=[CH:22][CH:23]=3)[CH:16]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1.Cl>C(O)C.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([CH:24]([C:26]4[C:31]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:29]=[CH:28][N:27]=4)[OH:25])[CH:21]=[CH:22][CH:23]=3)[CH:16]=2)[NH:11][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59824986{3-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-(3-trifluoromethyl-pyridin-2-yl)-methanol

Product 1

HCID 59824848{3-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-(3-trifluoromethyl-pyridin-2-yl)-methanolYield 49%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 14798
Sodium Hydroxide
Solvent

Procedure

390 mg (0.62 mmol) of {3-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-(3-trifluoromethyl-pyridin-2-yl)-methanol was dissolved in ethanol under gentle warming. The resulting solution was diluted with 2 M aqueous sodium hydroxide (16-30% v/v) and the resulting mixture was left at room temperature for 16 h. The pH was adjusted to 8 by addition of concentrated aqueous hydrochloric acid and the resulting solution was extracted three times with chloroform. The combined organic phases were dried over sodium sulfate and evaporated to afford 144 mg (0.30 mmol, 49%) of {3-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-(3-trifluoromethyl-pyridin-2-yl)-methanol as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 11.93 (d, 1H), 8.86 (d, 1H), 8.49 (d, 1H), 8.20 (dd, 1H), 8.11 (d, 1H), 7.75 (s, br., 1H), 7.73 (d, 1H), 7.58 (d(m), 1H), 7.56 (d, 1H), 7.54 (dd, 1H), 7.40 (t, 1H), 7.32-7.29 (m, 2H), 7.15 (dd, 1H), 7.05 (dd, 1H), 6.23 (d, 1H), 6.09 (d, 1H), 3.82 (s, 3H); MS: m/z 476.1 (M+H+).

Workup

  1. extractionthe resulting solution was extracted three times with chloroform
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-cb7d5a64c36e4021b36071ba7df6a2c0
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08242280B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes