2-Bromoethanol → HCID 90031775, compound

HRID 531889Notes

Reaction equation

HRID 531889 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:44]=[CH:45][CH:46]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([N:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)[CH:22]=4)[CH:19]=3)[N:14]([S:33]([C:36]3[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=3)(=[O:35])=[O:34])[CH:13]=2)[C:8]([CH3:43])=[N:7]1.Br[CH2:48][CH2:49][OH:50].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:44]=[CH:45][CH:46]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[C:23]([N:27]5[CH2:28][CH2:29][N:30]([CH2:48][CH2:49][OH:50])[CH2:31][CH2:32]5)[CH:24]=[CH:25][CH:26]=4)[CH:19]=3)[N:14]([S:33]([C:36]3[CH:37]=[CH:38][C:39]([CH3:40])=[CH:41][CH:42]=3)(=[O:34])=[O:35])[CH:13]=2)[C:8]([CH3:43])=[N:7]1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 118524080HCID 118524080, compound

Product 1

HCID 90031775HCID 90031775, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using the same reaction conditions as described in step-ii of example-35, 3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(3-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (70 mg, 0.104 mmol) was alkylated with 2-bromoethanol (13 mg, 0.104 mmol) using potassium carbonate (73 mg, 0.522 mmol), DMF (2 ml) to yield 60 mg (84.5%) of the titled compound. MS: m/z=679.3 (M+1).

Workup

  1. customthe same reaction conditions

Sources & evidence

ORD record
ord-ab7dc45f23954018be79806191425b14
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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