Sodium Carbonate → HCID 90030381, compound

HRID 531689Notes

Reaction equation

HRID 531689 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=4)[CH:15]=3)=[CH:9][N:8]([S:24]([C:27]3[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:5]2=[N:6][CH:7]=1.[CH3:34][S:35]([NH:38][C:39]1[CH:44]=[C:43](B2OC(C)(C)C(C)(C)O2)[CH:42]=[CH:41][C:40]=1[N:54]1[CH2:59][CH2:58][N:57]([CH2:60][C:61]([NH2:63])=[O:62])[CH2:56][CH2:55]1)(=[O:37])=[O:36].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.CO.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][N:14]1[CH:15]=[C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:43]4[CH:42]=[CH:41][C:40]([N:54]5[CH2:55][CH2:56][N:57]([CH2:60][C:61]([NH2:63])=[O:62])[CH2:58][CH2:59]5)=[C:39]([NH:38][S:35]([CH3:34])(=[O:36])=[O:37])[CH:44]=4)[CH:3]=3)[N:8]([S:24]([C:27]3[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH:9]=2)[CH:12]=[N:13]1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 90022686HCID 90022686, compound2×HCID 1182009745-bromo-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 90030381HCID 90030381, compoundYield 56.9%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 86587398Ethanol toluene waterSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-1, 5-bromo-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (compound of Step-i of example 9) (100 mg, 0.190 mmol) was coupled with 2-(4-(2-(methylsulfonamido)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazin-1-yl)acetamide (Intermediate 65A) 125 mg, 0.285 mmol) using sodium carbonate (60 mg, 0.567 mmol) and Pd(PPh3)4 (11 mg, 0.0095 mmol) in toluene/ethanol/water (2/2/1 mL). This afforded 82 mg (56.9% yield) after preparative TLC (Silicagel-1000 micron) using 5% ammoniated methanol in DCM as eluent. MS: m/z=757.2 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-600708e16f694618a63702811c5721ce
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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