Trifluoroacetic acid → HCID 59375081, compound

HRID 661992Notes

Reaction equation

HRID 661992 reaction equation
[Br:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([C:15]([OH:18])([CH3:17])[CH3:16])=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:5]([C:19]([NH2:21])=[O:20])=[CH:4][CH:3]=1.[C:22](O)(C(F)(F)F)=O>CO.C(Cl)Cl>[Br:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([C:15]([O:18][CH3:22])([CH3:17])[CH3:16])=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:5]([C:19]([NH2:21])=[O:20])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66605841HCID 66605841, compound2×

Product 1

HCID 59375081HCID 59375081, compoundYield 179.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide (Intermediate 73-2, 120 mg, 0.346 mmol) and TFA (0.013 mL, 0.173 mmol) in methanol (2 mL) was stirred at rt over a weekend. The mixture was diluted with DCM, washed with 1 M aqueous sodium hydroxide and water, dried and concentrated. The residue was combined with that from another reaction done with 20 mg of Intermediate 73-2, and purified by column chromatography (eluting with hexane-EtOAc) to provide 4-bromo-7-(2-methoxypropan-2-yl)-9H-carbazole-1-carboxamide as a white solid (112 mg, 77%). 1H NMR (400 MHz, chloroform-d) δ 10.53 (1H, br. s.), 8.68 (1H, d, J=8.36 Hz), 7.59 (1H, d, J=1.10 Hz), 7.36-7.44 (3H, m), 3.13 (3H, s), 1.64 (6H, s). Mass spectrum m/z 361, 363 (M+H)+.

Workup

  1. washwashed with 1 M aqueous sodium hydroxide and water
  2. customdried
  3. concentrationconcentrated
  4. custompurified by column chromatography (eluting with hexane-EtOAc)

Sources & evidence

ORD record
ord-2ec6cc42b4884c2f9688a812ee38ea72
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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