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

HRID 531798Notes

Reaction equation

HRID 531798 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[CH:13][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)=[N:15][CH:16]=3)[CH:9]=2)[N:4]([S:30]([C:33]2[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[CH:3]=1.[CH2:40]([O:47][C:48]1[CH:49]=[C:50]([CH:66]=[CH:67][CH:68]=1)[CH2:51][N:52]1[CH:56]=[C:55](B2OC(C)(C)C(C)(C)O2)[CH:54]=[N:53]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=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]>[CH2:40]([O:47][C:48]1[CH:49]=[C:50]([CH:66]=[CH:67][CH:68]=1)[CH2:51][N:52]1[CH:56]=[C:55]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:12]=[CH:13][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)=[N:15][CH:16]=4)[CH:9]=3)[N:4]([S:30]([C:33]3[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[CH:3]=2)[CH:54]=[N:53]1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 894985761-(3-(benzyloxy)benzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×HCID 118523942tert-butyl 4-(5-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazine-1-carboxylate2×

Product 1

HCID 90030878tert-butyl 4-(5-(3-(1-(3-(benzyloxy)benzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazine-1-carboxylateYield 69.2%

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-(5-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazine-1-carboxylate (Intermediate 66K) (300 mg, 0.454 mmol) was coupled with 1-(3-(benzyloxy)benzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 64E) (195 mg, 0.500 mmol) using sodium carbonate (145 mg, 1.364 mmol) and Pd(dppf)Cl2 (17 mg, 0.022 mmol) in toluene/ethanol/water (3/3/2 mL) to afford 250 mg (69% yield) of the titled compound after purification by column (Silica gel 60/120) using 0.5% methanol in DCM as eluent. MS: m/z=796.3 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-eb2734276b564a9da62947cedb980233
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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