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 1811334Notes

Reaction equation

HRID 1811334 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-62e4d60bc040478b8ab5037d9f8a0cef
Source dataset
uspto-grants-2013_01
Patent number
US08362251B2

Reaction notes

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