Sodium Carbonate → tert-butyl 4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-nitrophenyl)piperazine-1-carboxylate

HRID 531678Notes

Reaction equation

HRID 531678 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)=[C:13]([N+:30]([O-:32])=[O:31])[CH:12]=3)[CH:9]=2)[N:4]([S:33]([C:36]2[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=2)(=[O:35])=[O:34])[CH:3]=1.[F:43][C:44]1[CH:45]=[C:46]([CH:62]=[CH:63][CH:64]=1)[CH2:47][N:48]1[CH:52]=[C:51](B2OC(C)(C)C(C)(C)O2)[CH:50]=[N:49]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:43][C:44]1[CH:45]=[C:46]([CH:62]=[CH:63][CH:64]=1)[CH2:47][N:48]1[CH:52]=[C:51]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:16]=[CH:15][C:14]([N:17]5[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]5)=[C:13]([N+:30]([O-:32])=[O:31])[CH:12]=4)[CH:9]=3)[N:4]([S:33]([C:36]3[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=3)(=[O:35])=[O:34])[CH:3]=2)[CH:50]=[N:49]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 691327261-(3-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×HCID 90031353tert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-nitrophenyl)piperazine-1-carboxylate2×

Product 1

HCID 90030997tert-butyl 4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-nitrophenyl)piperazine-1-carboxylateYield 33.05%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

Using similar reaction conditions as described in step-i of example-1, tert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-nitrophenyl)piperazine-1-carboxylate (intermediate 66J) (340 mg, 0.48 mmol) was coupled with 1-(3-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 11) (189 mg, 0.628 mmol) using Pd(dppf)Cl2 (18 mg, 0.024 mol) and sodium carbonate (152 mg, 1.44 mmol) in toluene/ethanol/water (20/10/5 ml) to afford 120 mg (33.05% yield) of the titled. MS: m/z=752.2 (M+1).

Workup

  1. customreaction conditions
  2. customto afford 120 mg (33.05% yield) of the

Sources & evidence

ORD record
ord-216852020d814af5a6c583ff6563ca86
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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