Sodium Hydroxide → 2-{4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-N,N-dimethyl-2-hydroxy-acetamide

HRID 886575Notes

Reaction equation

HRID 886575 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:23]=[CH:22][N:21]=[C:20]([C:24](=[O:30])[C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH:19]=3)[CH:16]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1.[OH-].[Na+].[BH4-].[Na+]>C(O)C>[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:23]=[CH:22][N:21]=[C:20]([CH:24]([OH:30])[C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH:19]=3)[CH:16]=2)[NH:11][CH:10]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 4311764Sodium borohydrideHCID 598250242-{4-[3-(2-Methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-N,N-dimethyl-2-oxo-acetamide

Product 1

HCID 598249902-{4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-N,N-dimethyl-2-hydroxy-acetamideYield 14.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-{4-[3-(2-Methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-N,N-dimethyl-2-oxo-acetamide (100 mg, 0.18 mmol) was dissolved in ethanol (2.0 mL) and treated with 4 N aqueous sodium hydroxide (49.6 μL, 0.198 mmol). After 4 h, an additional 22.5 μL (0.09 mmol) 4 N aqueous sodium hydroxide was added. After 19 h, sodium borohydride (7.5 mg, 0.198 mmol) was added to the mixture at 0° C. After 55 min., the mixture was concentrated in vacuo and purified by preparative HPLC to afford 2-{4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-N,N-dimethyl-2-hydroxy-acetamide (10.2 mg, 14.1%). 1H-NMR (500 MHz, dimethylsulfoxide-d6) δ 2.85 (s, 3H), 3.00 (s, 3H), 3.82 (s, 3H), 5.53 (d, J=7.5 Hz, 1H), 5.95 (d, J=7.5 Hz, 1H), 7.06 (dt, J=7.0, J=1.0 Hz, 1H), 7.15 (br d, J=8.5 Hz, 1H), 7.27 (dd, J=1.0, J=5.0 Hz, 1H), 7.32 (dt, J=2.0, J=7.0 Hz, 1H), 7.56 (dd, J=1.0, J=8.0 Hz, 1H), 7.73 (d, J=3.0 Hz, 1H), 7.99 (br s, 1H), 8.58 (d, J=2.0 Hz, 1H), 8.62 (d, J=5.0 Hz, 1H), 8.94 (d, J=2.0 Hz, 1H), 11.99 (s, 1H). MS: m/z 403 (M+H+).

Workup

  1. waitAfter 19 h
  2. waitAfter 55 min.
  3. concentrationthe mixture was concentrated in vacuo
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-2e323d6fe2d54f05b50feb8ac87faee9
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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