Pyridine → 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 2-hydroxy-3-pyrrolidin-1-yl-propyl ester

HRID 1008122Notes

Reaction equation

HRID 1008122 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1/[CH:8]=[C:9]1\[C:10](=[O:21])[N:11]([C:18](Cl)=[O:19])[C:12]2[C:17]\1=[CH:16][CH:15]=[CH:14][CH:13]=2.[N:22]1([CH2:27][CH:28]([OH:31])[CH2:29][OH:30])[CH2:26][CH2:25][CH2:24][CH2:23]1.N1C=CC=CC=1>C1COCC1>[OH:31][CH:28]([CH2:27][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:29][O:30][C:18]([N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)/[C:9](=[CH:8]/[C:3]2[NH:4][C:5]([CH3:7])=[CH:6][C:2]=2[CH3:1])/[C:10]1=[O:21])=[O:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1744523-(1-Pyrrolidinyl)propane-1,2-diolHCID 879046953-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carbonyl chloride

Product 1

HCID 601112253-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 2-hydroxy-3-pyrrolidin-1-yl-propyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a reaction mixture of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carbonyl chloride (150 mg, 0.5 mmol) and 3-pyrrolidin-1-yl-propane-1,2-diol (88 mg, 0.6 mmol) in 3.0 mL of THF was added 80 μl of pyridine dropwise at room temperature. Upon addition, the reaction mixture was stirred at room temperature for 20 min., and filtered. The orange solid was then washed with ethyl acetate and hexane sequentially and dried in a vacuum oven overnight to give 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 2-hydroxy-3-pyrrolidin-1-yl-propyl ester as an orange solid. 1HNMR (400 MHz, CDCl3 and 2 drops of DMSO-d6) δ 12.63 (s, br, 1H, NH-1′), 11.77 (s, br, 1H, OH), 7.86-7.88 (m, 1H), 7.51-7.53 (m, 1H), 7.42 (s, 1H, H-vinyl), 7.18-7.25 (m, 2H), 6.06 (d, J=2.3 Hz, 1H, H-4′), 4.65-4.73 (m, 2H), 4.44-4.56 (m, 2H), 3.91-3.93 (m, 1H), 3.33-3.52 (m, 2H), 2.88-3.15 (m, 2H), 2.40 (s, 3H, CH3), 2.36 (s, 3H, CH3), and 2.01-2.32 (m, 4H).

Workup

  1. additionUpon addition
  2. filtrationfiltered
  3. washThe orange solid was then washed with ethyl acetate and hexane sequentially
  4. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-969bee4082194c7ea4453567f3a53dd2
Source dataset
uspto-grants-2004_09
Patent number
US06797725B2

Reaction notes

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