Triethylamine → 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 531737Notes

Reaction equation

HRID 531737 reaction equation
COC1C=CC(B2OC(C)(C)C(C)(C)O2)=CC=1[CH2:18][S:19](N)(=[O:21])=[O:20].[F:23][C:24]1[CH:25]=[C:26]([CH:64]=[CH:65][CH:66]=1)[CH2:27][N:28]1[CH:32]=[C:31]([C:33]2[C:41]3[C:36](=[N:37][CH:38]=[C:39]([C:42]4[CH:47]=[CH:46][C:45]([N:48]5[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]5)=[CH:44][CH:43]=4)[CH:40]=3)[N:35]([S:54]([C:57]3[CH:63]=[CH:62][C:60]([CH3:61])=[CH:59][CH:58]=3)(=[O:56])=[O:55])[CH:34]=2)[CH:30]=[N:29]1.CS(Cl)(=O)=O.C(N(CC)CC)C>C(Cl)Cl>[F:23][C:24]1[CH:25]=[C:26]([CH:64]=[CH:65][CH:66]=1)[CH2:27][N:28]1[CH:32]=[C:31]([C:33]2[C:41]3[C:36](=[N:37][CH:38]=[C:39]([C:42]4[CH:47]=[CH:46][C:45]([N:48]5[CH2:49][CH2:50][N:51]([S:19]([CH3:18])(=[O:21])=[O:20])[CH2:52][CH2:53]5)=[CH:44][CH:43]=4)[CH:40]=3)[N:35]([S:54]([C:57]3[CH:63]=[CH:62][C:60]([CH3:61])=[CH:59][CH:58]=3)(=[O:55])=[O:56])[CH:34]=2)[CH:30]=[N:29]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 900312383-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 1317356682-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl methane sulfonamide

Product 1

HCID 1185240533-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineYield 71.42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using similar reaction conditions as described in step i of intermediate 17, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (product of step 1 of example 124) (75 mg, 0.123 mmol) was mesylated with methane sulfonyl chloride (17 mg, 0.148 mol) using triethylamine (35 μL, 0.247 mmol) in DCM (5 mL) to afford 60 mg (71.42% yield) of the titled compound. MS: m/z=685.1 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-80bf6d3823c347b192ba9c5580aeb929
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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