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Water → 6-fluoro-5-[(S)-(pyrrolidin-3-ylsulfanyl)]-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one

HRID 1633800
Notes
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Reaction equation

HRID 1633800 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([S:13][C:14]2[CH:15]=[C:16]([C:28]3[NH:29][CH:30]=[CH:31][CH:32]=3)[C:17]3[C:18](=[O:27])[NH:19][C:20]4[C:25]=3[C:24]=2[C:23]([F:26])=[CH:22][CH:21]=4)[CH2:9]1)=O)(C)(C)C.O>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:26][C:23]1[C:24]2[C:25]3[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:27])[C:17]=3[C:16]([C:28]1[NH:29][CH:30]=[CH:31][CH:32]=1)=[CH:15][C:14]=2[S:13][C@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 962WaterHCID 12042976(S)-3-[6-fluoro-2-oxo-3-(1H-pyrrol-2-yl)-1,2-dihydro-benzo[cd]indol-5-ylsulfanyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 100666566-fluoro-5-[(S)-(pyrrolidin-3-ylsulfanyl)]-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 6422
Trifluoroacetic acid
Solvent

Procedure

(S)-3-[6-Fluoro-2-oxo-3-(1H-pyrrol-2-yl)-1,2-dihydro-benzo[cd]indol-5-ylsulfanyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (from Example 56 above) (54 mg, 0.12 mmol) was dissolved at 0° C. in a 50% TFA in CH2Cl2 solution (6 mL) that contained H2O (0.3 mL). After 2 hours the reaction mixture was partitioned between ethyl acetate and aqueous 1N NaOH. The pH of the aqueous layer was adjusted to 14. The aqueous layer was extracted twice with ethyl acetate and the combined organic layer was washed with H2O, dried over Na2SO4, filtered, and concentrated to dryness. The residue was purified by a precipitation out of THF with excess of pentane to give 6-fluoro-5-[(S)-(pyrrolidin-3-ylsulfanyl)]-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one as a yellow solid. (Yield 41 mg; 97%).

Workup

  1. customAfter 2 hours the reaction mixture was partitioned between ethyl acetate and aqueous 1N NaOH
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. washthe combined organic layer was washed with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by a precipitation out of THF with excess of pentane

Sources & evidence

ORD record
ord-11309eff12434505a39e25f8c60b1297
Source dataset
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06504034B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes