Methanethiol → HCID 10297616, compound

HRID 857356Notes

Reaction equation

HRID 857356 reaction equation
[CH3:1][SH:2].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[C:19]3[C:18]([CH:20](O)[CH3:21])=[CH:17][C:16]([F:23])=[CH:15][C:14]=3[N:13]3[CH2:24][CH2:25][CH:26]([CH2:27][C:28]([OH:30])=[O:29])[C:12]=23)=[CH:6][CH:5]=1>[I-].[Zn+2].[I-]>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[C:19]3[C:18]([CH:20]([S:2][CH3:1])[CH3:21])=[CH:17][C:16]([F:23])=[CH:15][C:14]=3[N:13]3[CH2:24][CH2:25][CH:26]([CH2:27][C:28]([OH:30])=[O:29])[C:12]=23)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 878MethanethiolHCID 10112823HCID 10112823, compound

Product 1

HCID 10297616HCID 10297616, compound

Reagents, catalysts & solvents 1

HCID 9883512zinc(II)iodideCatalyst

Conditions

Temperature
0 °C

Procedure

Methanethiol was bubbled into a solution of [9-[(4-chlorophenyl)-sulfanyl]-6-fluoro-8-(1-hydroxyethyl)-2,3-dihydro-1H-pyrrolo [1,2-a]indol-1-yl]acetic acid (Example 15A, Step 1, 48 mg, 0.1 mmol) in 5 mL of dichloro'methane at 0° C. and zinc iodide (5 mg, 0.015 mmol) was added. The reaction mixture was stirred at 0° C. for 15 minutes and quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by preparative HPLC with a C18 Zorbax column using a mixture of 5% iPrOH in hexanes+0.2% AcOH as eluant to provide the title compound as a white solid foam.

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC with a C18 Zorbax column
  6. additiona mixture of 5% iPrOH in hexanes+0.2% AcOH as eluant

Sources & evidence

ORD record
ord-2552ade0cfb34ce4933ae144582b3763
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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