Sodium Carbonate → HCID 59971444, compound

HRID 382047Notes

Reaction equation

HRID 382047 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([OH:3])=[O:2].I[C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1/[C:16](=[CH:24]/[C:25]1[NH:26][CH:27]=[CH:28][C:29]=1[O:30][CH3:31])/[C:17](=[O:23])[NH:18]2.C([O-])([O-])=O.[Na+].[Na+]>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.COCCOC>[CH3:31][O:30][C:29]1[CH:28]=[CH:27][NH:26][C:25]=1/[CH:24]=[C:16]1\[C:17](=[O:23])[NH:18][C:19]2[C:15]\1=[C:14]([C:7]1[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=1)[CH:22]=[CH:21][CH:20]=2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 15548053(Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one2×

Product 1

HCID 59971444HCID 59971444, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Using Method S above, 4-carboxy-phenyl boronic acid (27.2 mg, 0.164 mmol) (Lancaster) was coupled with (Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (50 mg, 0.137 mmol) (Starting Material 3) using (Ph3P)4Pd (4.8 mg) (Aldrich) as catalyst in DME (5 mL) and solid Na2CO3 (51 mg, 0.48 mmol) at reflux for 18 h to give (Z)-4-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-4-yl]-benzoic acid (yield: 15 mg, 31%).

Sources & evidence

ORD record
ord-0c84d0d9cbbc418b98de9f52a517a13a
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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