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Sodium Carbonate → 6-(N-(4-bromobutyl)methylsulfonamido)-5-cyclopropyl-N-methyl-2-(p-tolyl)furo[2,3-b]pyridine-3-carboxamide

HRID 2190197
Notes
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Reaction equation

HRID 2190197 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:11]1[N:16]=[C:15]2[O:17][C:18]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)=[C:19]([C:20]([NH:22][CH3:23])=[O:21])[C:14]2=[CH:13][C:12]=1I)[S:7]([CH3:10])(=[O:9])=[O:8].CO[C:34]1C=CC=C(OC)[C:39]=1[C:40]1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C(=O)([O-])[O-].[Na+].[Na+].C1(B(O)O)CC1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:11]1[N:16]=[C:15]2[O:17][C:18]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)=[C:19]([C:20]([NH:22][CH3:23])=[O:21])[C:14]2=[CH:13][C:12]=1[CH:40]1[CH2:39][CH2:34]1)[S:7]([CH3:10])(=[O:9])=[O:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 580522976-(N-(4-bromobutyl)methylsulfonamido)-5-iodo-N-methyl-2-(p-tolyl)furo[2,3-b]pyridine-3-carboxamide

Product 1

HCID 545758766-(N-(4-bromobutyl)methylsulfonamido)-5-cyclopropyl-N-methyl-2-(p-tolyl)furo[2,3-b]pyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×

Procedure

To 6-(N-(4-bromobutyl)methylsulfonamido)-5-iodo-N-methyl-2-(p-tolyl)furo[2,3-b]pyridine-3-carboxamide (57 mg, 0.092 mmol) was added a premixed solution of S-Phos (3.77 mg, 9.19 μmol) and Pd(OAc)2 (0.825 mg, 3.68 μmol) in toluene (300 μL). Added a premixed solution of 2N SODIUM CARBONATE (919 μL, 1.838 mmol) and cyclopropylboronic acid (118 mg, 1.378 mmol) in toluene (900 μL). Degassed with N2 for 60 minutes.

Workup

  1. customDegassed with N2 for 60 minutes

Sources & evidence

ORD record
ord-117224c4e05d4dd58baece7659908d82
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08324239B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes