Water → 5-(2-Diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-hydroxymethyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

HRID 2365138Notes

Reaction equation

HRID 2365138 reaction equation
Br[CH:2]1[CH2:7][N:6]([CH2:8][CH2:9][N:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:5](=[O:15])[C:4]2[C:16]([CH3:31])=[C:17]([CH:19]=[C:20]3[C:28]4[C:23](=[CH:24][CH:25]=[C:26]([F:29])[CH:27]=4)[NH:22][C:21]3=[O:30])[NH:18][C:3]1=2.BrCC1C2C(=[O:50])N(CCN(CC)CC)CCC=2NC=1C=C1C2C(=CC=C(F)C=2)NC1=O.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH2:13]([N:10]([CH2:11][CH3:12])[CH2:9][CH2:8][N:6]1[CH2:7][CH2:2][C:3]2[NH:18][C:17]([CH:19]=[C:20]3[C:28]4[C:23](=[CH:24][CH:25]=[C:26]([F:29])[CH:27]=4)[NH:22][C:21]3=[O:30])=[C:16]([CH2:31][OH:50])[C:4]=2[C:5]1=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 666078287-Bromo-5-(2-diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-oneHCID 666082793-Bromomethyl-5-(2-diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

Product 1

HCID 666071455-(2-Diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-hydroxymethyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-oneYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7-bromo-5-(2-diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one and 3-bromomethyl-5-(2-diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one in 10 ml of methanol was added with saturated potassium carbonate (2 ml). The mixture was stirred at room temperature overnight, added with water (20 ml) and extracted with the 6 to 1 mixture of dichloromethane and methanol (10 ml×4). The combined extracts were concentrated to give 5-(2-diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-hydroxymethyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one (13 mg, 72%) as a yellow solid.

Workup

  1. extractionextracted with the 6 to 1 mixture of dichloromethane and methanol (10 ml×4)
  2. concentrationThe combined extracts were concentrated

Sources & evidence

ORD record
ord-99a21d9346314f4db85a0452b15af4f6
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

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