Sodium Methoxide → HCID 66604677, compound

HRID 2410696Notes

Reaction equation

HRID 2410696 reaction equation
C([O:4][CH2:5][C:6]1[CH:18]=[CH:17][C:16]2[C:15]3[C:10](=[C:11]([C:27](=[O:29])[NH2:28])[CH:12]=[C:13]([C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=4)[CH:14]=3)[NH:9][C:8]=2[CH:7]=1)(=O)C.C[O-].[Na+]>CO.CN(C=O)C>[Cl:26][C:21]1[CH:20]=[C:19]([C:13]2[CH:12]=[C:11]([C:27]([NH2:28])=[O:29])[C:10]3[NH:9][C:8]4[C:16]([C:15]=3[CH:14]=2)=[CH:17][CH:18]=[C:6]([CH2:5][OH:4])[CH:7]=4)[CH:24]=[CH:23][C:22]=1[Cl:25]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 66605310HCID 66605310, compound

Product 1

HCID 66604677HCID 66604677, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

(8-Carbamoyl-6-(3,4-dichlorophenyl)-9H-carbazol-2-yl)methyl acetate (150 mg, 0.211 mmol, Example 139) was dissolved in a mixture of MeOH (3 mL) and DMF (6 mL). To this solution was added sodium methanolate (140 mg, 0.648 mmol) and the reaction left stirring for 0.5 h. The product was isolated by preparative HPLC (100×30 mm Luna C18 column, flow rate 42 ml permin, gradient elution starting with A:B=90:10 and ending with A:B=30:70 [A=10 mM NH4OAc in 5% aqueous acetonitrile; B=10 mM NH4OAc in 95% aqueous acetonitrile] over 20 min) followed by removal of solvent to afford 39 mg of 3-(3,4-dichlorophenyl)-7-(hydroxymethyl)-9H-carbazole-1-carboxamide as a light yellow solid. MS (ESI) m/z 383.1 (M−H). 1H NMR (DMSO-d6) δ ppm 11.44 (1H, s), 8.73 (1H, d, J=1.53 Hz), 8.36 (1H, br. s.), 8.30 (1H, d, J=1.53 Hz), 8.22 (1H, d, J=2.14 Hz), 8.19 (1H, d, J=7.93 Hz), 7.94 (1H, dd, J=8.55, 2.14 Hz), 7.77 (1H, d, J=8.24 Hz), 7.71 (1H, s), 7.56 (1H, br. s.), 7.18 (1H, d, J=7.93 Hz), 5.24 (1H, t, J=5.80 Hz), 4.66 (2H, d, J=5.80 Hz).

Workup

  1. waitthe reaction left
  2. customThe product was isolated by preparative HPLC (
  3. wash100×30 mm Luna C18 column, flow rate 42 ml permin, gradient elution
  4. customB=10 mM NH4OAc in 95% aqueous acetonitrile] over 20 min) followed by removal of solvent

Sources & evidence

ORD record
ord-88412d244e544c1d809dc5174caf76c5
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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